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Here is a chemical reaction formula: Reactants are m2:CS(=O)C, amount is: 0.0 ;m3:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CCO)C2=C(C=CC=C2)Cl)C1, amount is: 0.0 ;m9_m1:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:ClCCl, amount is: 0.0 ;m6:C(C)N(CC)CC, amount is: 0.0 ;m5:O, amount is: 0.0 ;m4:ClCCl, amount is: 0.0 ;m9_m1:ClCCl, amount is: 0.0 ;m8:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC=O)C2=C(C=CC=C2)Cl)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 25 ml of dichloromethane solution containing 0.70 ml of oxalyl chloride was added 5 ml of dichloromethane solution containing 0.71 ml of dimethylsulfoxide at -78° C., followed by stirring for 5 minutes. To the solution was slowly added 10 ml of dichloromethane solution containing 1.69 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol obtained in Example 160, followed by stirring for 15 minutes at -78° C. To the reaction mixture was added 2.79 ml of triethylamine and the mixture was further stirred for one hour at 0° C. and for 1.5 hours at room temperature. After the addition of 100 ml of water, extraction was performed with 100 ml of dichloromethane. The dichloromethane layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure. The residue was purified by column chromatography using silica gel (eluent, hexane:ethyl acetate=1:1) to give 1.08 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde as light-yellow crystals, m.p. 173° to 176° C. |
Here is a chemical reaction formula: Reactants are m1_m3:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)O)C2=C(C=CC=C2)OC)C1, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)[O-])C2=C(C=CC=C2)OC)C1.[Na+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of (3R,5S)-7-chloro-5-(2-methoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (12 g) in methanol (200 ml) was added 1N aqueous sodium hydroxide (27.7 ml). After the acid was dissolved completely, the mixture was concentrated in vacuo. To the residue was added ethyl acetate (200 ml) and the mixture was concentrated in vacuo. The deposited crystals were collected to give sodium (3R,5S)-7-chloro-5-(2-methoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (11.8 g) as colorless crystals (mp>300° C.). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:BrC1=C(C=C(C=C1)O)OC, amount is: 0.0 ;m1_m2_m3_m4:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=CC(=C(C=C1)Br)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-bromo-3-methoxyphenol (21 g), benzyl bromide (13.5 ml), potassium carbonate (21.4 g) and acetone (200 ml) was stirred at room temperature for 24 h. The insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 4-benzyloxy-2-methoxybromobenzene (25 g) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:NC1=C(C(=O)C2=C(C=C(C=C2)OCC2=CC=CC=C2)OC)C=C(C=C1)Cl, amount is: 0.0 ;m1_m3_m2:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=C(C(C2=C(C=C(C=C2)OCC2=CC=CC=C2)OC)O)C=C(C=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-amino-4'-benzyloxy-5-chloro-2'-methoxybenzophenone (10 g) in methanol (100 ml) was added sodium borohydride (1.4 g). After being stirred for 24 h, the mixture was concentrated in vacuo. The residue was diluted with water (200 ml) and extracted with ethyl acetate (300 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-2:1) to give 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g) as colorless crystals (mp=101°-103° C.). |
Here is a chemical reaction formula: Reactants are m4:C(#N)[BH3-].[Na+], amount is: 0.0 ;m1_m2_m3_m5:NC1=C(C(C2=C(C=C(C=C2)OCC2=CC=CC=C2)OC)O)C=C(C=C1)Cl, amount is: 0.0 ;m1_m2_m3_m5:C(C(C)(C)C)=O, amount is: 0.0 ;m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=CC(=C(C=C1)C(C1=C(C=CC(=C1)Cl)NCC(C)(C)C)O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-amino-α-(4-benzyloxy-2-methoxyphenyl)-5-chlorobenzyl alcohol (9.5 g), pivalaldehyde (3.35 ml), acetic acid (1.85 g) and ethanol (200 ml) was stirred for 30 min. To the mixture was added sodium cyanoborohydride (2.33 g) and the mixture was stirred for 24 h. After the mixture was concentrated in vacuo, the residue was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give α-(4-benzyloxy-2-methoxyphenyl)-2-neopentylamino-5-chlorobenzyl alcohol (10.0 g) as a colorless oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=CC(=C(C=C1)N(C(=O)C=CC(=O)OCC)CC(C)(C)C)C(C1=C(C=C(C=C1)OCC1=CC=CC=C1)OC)O, amount is: 0.0 ;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=CC(=C(C=C1)[C@H]1O[C@@H](C(N(C2=C1C=C(C=C2)Cl)CC(C)(C)C)=O)CC(=O)OCC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of ethyl 3-[N-[4-chloro-2-(4-benzyloxy-α-hydroxy-2-methoxybenzyl)-phenyl]-N-neopentylcarbamoyl]acrylate (12 g), potassium carbonate (5.9 g) and ethanol (150 ml) was stirred for 24 h. After the mixture was concentrated in vacuo, the residue was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give ethyl trans-5-(4-benzyloxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (9.8 g) as needles (mp=130°-131° C.). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)OCC)C2=C(C=C(C=C2)O)OC)C1, amount is: 0.0 ;m1_m2_m3_m4:C(C)I, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)OCC)C2=C(C=C(C=C2)OCC)OC)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl trans-7-chloro-5-(4-hydroxy-2-methoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (0.25 g), ethyl iodide (0.06 ml), potassium carbonate (0.15 g) and N,N-dimethylformamide (200 ml) was stirred for 3 h. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (100 ml). The extract was washed with 1N hydrochloric acid and aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated in vacuo to give ethyl trans-7-chloro-5-(4-ethoxy-2-methoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (0.24 g) as colorless crystals (mp=164°-166° C.). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:C(C)OC1=CC(=C(C=C1)[C@H]1O[C@@H](C(N(C2=C1C=C(C=C2)Cl)CC(C)(C)C)=O)CC(=O)OCC)OC, amount is: 0.0 ;m1_m2_m3_m4_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4_m5:CO, amount is: 0.0 ;m1_m2_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC1=CC(=C(C=C1)[C@H]1O[C@@H](C(N(C2=C1C=C(C=C2)Cl)CC(C)(C)C)=O)CC(=O)O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl trans-5-(4-ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetate (0.18 g), potassium carbonate (0.10 g), methanol (10 ml), tetrahydrofuran (10 ml) and water (5 ml) was refluxed for 1.5 h. The resulting mixture was concentrated in vacuo, acidified with 1N hydrochloric acid (50 ml) and extracted with ethyl acetate (50 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo to give trans-5-(4-ethoxy-2-methoxyphenyl)-7-chloro-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid as colorless crystals (mp=230°-232° C.). |
Here is a chemical reaction formula: Reactants are m2:[OH-].[NH4+], amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE;m1_m4:C(#N)C1=NNC(=C1SC(F)(F)F)NC(C(F)(F)F)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m4:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(#N)C1=NNC(=C1SC(F)(F)F)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The product of Step E (55 g, 181 mmoles) was dissolved in methanol. 100 ml of ammonium hydroxide were added, the solution was refluxed for 3 hours and then stirred at room temperature for 15 hours. The methanolic solution was brought to pH7 using concentrated aqueous hydrochloric acid and diluted with ethyl acetate. The organic layer was washed several times with water and brine, dried over MgSO4 and concentrated to dryness to give an oily brown residue which was recrystallized from methyl tert-butyl ether to afford 33 g of the title compound, m.p. around 187° C. |
Here is a chemical reaction formula: Reactants are m3_m7:C(C)OC1=CC=C(N)C=C1, amount is: 0.0 ;m2_m6:ClCl, amount is: 0.0 ;m1_m5:CCC(=S)OCC, amount is: 0.0 ;m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:C(Cl)Cl, amount is: 0.0 ;m2_m6:C(Cl)Cl, amount is: 0.0 ;m1_m5:C(Cl)Cl, amount is: 0.0 ;m8:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OC=1C=C2CC(NC2=CC1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 23.6 g of ethyl methylthioacetate in 60 ml of DCM are added to a solution, cooled to about -70° C., of 12.5 g of chlorine in 400 ml of DCM. After stirring for 5 minutes at the same temperature, a solution of 4-ethoxyaniline (48.3 g) in 120 ml of DCM is added. The mixture is stirred for one hour at about -70° C., 39.3 ml of triethylamine are added and the resulting mixture is allowed to warm up to room temperature. 200 ml of water are added and the organic phase is decanted, dried over magnesium sulfate and evaporated under reduced pressure. The residue is taken up with 500 ml of isopropanol and 20 ml of concentrated hydrochloric acid. The mixture is stirred for about 16 hours at room temperature and filtered and the precipitate is separated off. The filtrate is concentrated under reduced pressure to give the expected product. |
Here is a chemical reaction formula: Reactants are m1_m2:FC1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m1_m2:C(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=CC=C(C(=O)OCC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture containing 35 g of 4-fluorobenzoyl chloride in 50 ml of 100% ethanol is refluxed for 15 minutes. 35 g of the ethyl 4-fluorobenzoate obtained are mixed with 22 g of imidazole and 61 g of potassium carbonate in 35 ml of DMSO. The mixture is heated for 18 hours at 120°-130° C. and 500 ml of iced water are then added. A precipitate forms and the expected product crystallizes from iso ether. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 ;m1_m6_m2:OC=1C=CC(=NC1)C, amount is: 0.0 ;m1_m6_m2:OO, amount is: 0.0 ;m3:OO, amount is: 0.0 ;m5:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6_m2:C(C)(=O)O, amount is: 0.0 ;m7:N1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(=O)C1=NC=C(C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 21.8 g of 5-hydroxy-2-picoline (0.2 mol) in 200 mL of glacial acetic acid was added 18 mL of 30% hydrogen peroxide (0.159 mol) in one portion. The mixture was heated in an oil bath at 80°-85° C. with stirring for 3 h. Then another 18 mL of hydrogen peroxide was added and the mixture was stirred for 3 h at the same temperature. Excess solvent was removed in vacuo followed by the addition of acetone, which caused the pyridine N-oxide to crystallize. Without further purification, 200 mL of acetic anhydride was added to the solid and the mixture was heated at 120° C. with stirring in an oil bath for 2 h. After cooling to room temperature, excess acetic anhydride was removed by high vacuum distillation. The oily material was again oxidized with 30% hydrogen peroxide twice and rearranged with acetic anhydride following the same procedure and amounts depicted above. The black oily material obtained was hydrolyzed with 200 mL of 1N HCl (0.2 mol) at room temperature for 3 weeks (hydrolysis at higher temperature may be harmful to the pyridine nucleus). The mixture was neutralized with anhydrous sodium carbonate, indicated by litmus paper and then extracted three times with 300 mL of diethylether. The combined ether extracts were dried (MgSO4), filtered and evaporated to leave a solid material in a small mount of oil. The pure product (7.8 g, 32%) was obtained by filtering the solid, followed by washing it with a small amount of ether. It is yellow in color and shows a sharp melting point at 186°-187° C. 1H NMR (d6 -DMSO) d: 11.i0 (br. s, 1H, OH); 9.87 (s, 1H, CHO); 8.35 (d, J=2Hz, 1H); 7.58 (d, J=9 Hz, 1H); 7.35 (d of d, J=2Hz, 9Hz, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C1(=CC=CC=C1)NC(NN)=O, amount is: 0.0 ;m1_m2_m3:OC=1C(=NC=CC1)C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O.C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC=1C(=NC=CC1)C=NNC(=O)NC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Phenyl semicarbazide (4.91 g, 33 mmol) was added to a suspension of 3-hydroxy-2-pyridine carbaldehyde (4.0 g, 33 mmol) in a mixture of ethanol water (30 mL:40 mL). The reaction mixture was stirred at room temperature for 3 h and the yellow product was collected by filtration. The yellow precipitate was washed with EtOH/H2O 1:1 and dried under P2 O5 to yield 8.22 g (99%) of product. It can be recrystallized from EtOH/H2O; m.p. 201°-2° C. (dec.). 1H NMR (d6 -DMSO) d: 10.85 (br.s., 1H); 10.6 (br.s., 1H); 9.14 (s, 1H); 8.27 (s, 1H); 8.15 (d 9f d, 1H); 7.55 (d, 2H); 7.26-7.36 (m, 4H); 7.01 (t, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:OC=1C(=NC(=CC1)C)CO, amount is: 0.0 ;m1_m2_m3:[Se](=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(C)O, amount is: 0.0 ;m1_m2_m3:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC=1C(=NC(=CC1)C)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Hydroxy-6-methyl-2-pyridine methanol (20.0 g, 0.14 mol) and selenium dioxide(8.0 g, 72 mmol) were dissolved in 140 mL of 1,4-dioxane and 280 mL of absolute ethanol. The resulting mixture was heated at 80°-85° C. for 12 h. The selenium precipitate was removed by filtration and the filtrate was concentrated to dryness in vacuo. The dark red residue was sublimed at 90° C. and 14 mmHg for 6 h to obtain 11.0 g (56%) of pure product, m.p. 101°-102° C.; 1H NMR (CDCl3) δ: 10.50 (br s, 1H), 10.03 (s, 1H), 7.27 (s, 2H); 2.53 (s, 3H). |
Here is a chemical reaction formula: Reactants are m4:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE;m3:BrCC1=C(C(=O)OC)C=CC=C1, amount is: 0.0 ;m1_m5_m2:C(C)(=O)NC=1C=C(C=CC1)O, amount is: 0.0 ;m1_m5_m2:C([O-])([O-])=O.[Cs+].[Cs+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)NC=1C=C(OCC2=C(C(=O)OC)C=CC=C2)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-acetamidophenol (1.0 g, 6.6 mmol) in dimethylformamide (10 ml) was added cesium carbonate (1.3 g, 3.9 mmol), followed by stirring at room temperature for 30 minutes. To the resulting mixture was added methyl 2-bromomethylbenzoate (1.8 g, 7.9 mmol), and the mixture was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was poured into a5% aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), followed by trituration with hexane to give methyl 2-(3-acetamidophenoxymethyl)benzoate as a white solid (1.21 g, 61%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:BrCC1=C(SC=C1)C(=O)OC, amount is: 0.0 ;m1_m3_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Br-].COC(=O)C=1SC=CC1C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of methyl 3-bromomethyl-2-thiophenecarboxylate (7.31 g, 31.1 mmol) in toluene (90 ml) was added triphenylphosphine (7.92 g, 30.2 mmol) under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 2 days. The precipitated crystals were collected by filtration and dried to give 2-methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromide (10.57 g, 70.4%). This product was subjected to the reaction of Reference Example 13 without purification. |
Here is a chemical reaction formula: Reactants are m1:CCCCC=1C=CC=CC1, amount is: 0.0 ;m2:C(=C)[Si](Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m3:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 .Products are 0:Cl[Si](Cl)(Cl)CCC1=C(C(=C(C(=C1CCCC)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl)CC[Si](Cl)(Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In the same apparatus and by the same procedure described in EXAMPLE 1, n-butylbenzene 0.86 g (6.40 mmol), vinyltrichlorosilane 5.17 g (32.00 mmol) and aluminum chloride 0.047 g (0.35 mmol) were reacted at 80° C. for 6 hours under a dry nitrogen atmosphere. Recrystallization of solid product from THF gave 6.16 g (yield: 2.68%, mp: 228°-35° C.) of pentakis(trichlorosilylethyl)-n-butylbenzene. Distillation of the filtrate gave 2.20 g (yield: 36.59%, bp: 192°-8° C./0.6 mm), 1.81 g (yield: 30.0%, bp: 220°-5° C./0-6 mm), 0.63 g (yield: 10.15%), 0.12 g (yield: 2.05%) and 0.22 g (yield: 3.59%) of tris-, tetrakis(trichlorosilylethyl)-n-butylbenzenes, tetrakis(trichlorosilylethyl)dibutylbenzene, mono- and bis(trichlorosilylethyl)benzenes, respectively. isomeric mixtures were also obtained. NMR data of the polyalkylated products prepared as above are listed in Table 13. |
Here is a chemical reaction formula: Reactants are m1_m2:C(=O)(O)CNCCO, amount is: 0.0 MOLE;m1_m2:C(CO)#N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(=O)(O)CN(CC#N)CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The hydrolysis of (I) with base gives N-carboxymethylamino-2-ethanol (II). Compound (II) is then reacted with additional glycolonitrile to form N-carboxymethyl-N-cyanomethylamino-2-ethanol (III). The molar ratio of (II) to glycolonitrile is generally about 1:1. In the above reactions, hydrogen cyanide and formaldehyde can be substituted for glycolonitrile. |
Here is a chemical reaction formula: Reactants are m3:C(C)(=O)[O-].[Na+], amount is: 0.0 MOLE;m1:C1(=C(NC(=O)NC1=O)[O-])N=C2C(=O)NC(=O)NC2=O.[NH4+], amount is: 0.0 MOLE;m0_m4_m6:O, amount is: 0.0 ;m2:C1(=C(NC(=O)NC1=O)O)N=C2C(=O)NC(=O)NC2=O.N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m0_m4_m6:[Cu](Cl)Cl, amount is: 0.0 MOLE;m5:[Cu], amount is: 0.0 MOLE.Products are 0:C(CO)N(CC(=O)O)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Copper titration value is used to measure the extent of biodegradation of the chelating agents during the procedure. Titration is performed using ammonium purpurate (indicator for complexometric titration, commercially available from Aldrich Chemical Co., Inc. under the trade designation Murexide) as the indicator at approximately pH 8, and using sodium acetate as buffer. Titration of 2.0 mg HEIDA (0.0105 moles) in 100 mL water with 0.01 molar copper chloride gives an endpoint of 1.06 mL, representing a 1:1 chelation of copper. Analysis is performed daily for a period of 28 days. |
Here is a chemical reaction formula: Reactants are m3_m4:CNCCO, amount is: 0.0 ;m1_m2:ClC=1C=C(C=O)C=CC1Cl, amount is: 0.0 ;m1_m2:C(#N)[Si](C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:CO, amount is: 0.0 ,Catalysts are m5:[I-].[Zn+2].[I-], amount is: 0.0 .Products are 0:ClC=1C=C(C=CC1Cl)C(C#N)N(C)CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 10 g of 3,4-dichlorobenzaldehyde and 9.5 ml of cyanotrimethylsilane is cooled in an ice bath, 0.01 g of zinc iodide is added and the mixture is stirred for 15 minutes at RT. A solution of 4.5 g of 2-(methylamino)ethanol in 50 ml of MeOH is then added and the reaction mixture is heated at 60° C. for 2 hours. After one night at RT, it is concentrated under vacuum, the residue is extracted with ether and the organic phase is washed with water, dried over MgSO4 and filtered. The filtrate is acidified to pH 1 by the addition of a saturated solution of hydrochloric acid in ether, acetone is added and the mixture is stirred until crystallization occurs. This gives 15 g of the expected product after wringing of the crystals formed. M.p.=130° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:CN(CC(OCCOC1OCCCC1)C1=CC(=C(C=C1)Cl)Cl)C(=O)OC(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(CC(OCCO)C1=CC(=C(C=C1)Cl)Cl)C(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.56 g of pyridinium paratoluenesulfonate is added to a solution of 10 g of the compound obtained in EXAMPLE 8, step C), in 100 ml of MeOH and the reaction mixture is refluxed for 1 hour 15 minutes. It is concentrated under vacuum and the residue is taken up with ether, washed with water and with a buffer solution of pH 2, dried over MgSO4 and concentrated under vacuum to give 8.2 g of the expected product, which is used as such in the next step. |
Here is a chemical reaction formula: Reactants are m1_m5:Cl.OC1(CCN(CC1)CCOC(CN(C(=O)OCC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1, amount is: 0.0 ;m4:CCCl, amount is: 0.0 MOLE;m2_m3:C(C)N(CC)CC, amount is: 0.0 ;m2_m3:C(CC)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(Cl)Cl, amount is: 0.0 ;m6:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:O.Cl.C1(=CC=CC=C1)C1(CCN(CC1)CCOC(CN(C(=O)OCC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)OC(CC)=O.C1(=CC=CC=C1)C1(CCN(CC1)CCOC(CN(C)C(=O)OCC1=CC=CC=C1)C1=CC(=C(C=C1)Cl)Cl)OC(CC)=O.Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 670 mg of the compound obtained in EXAMPLE 9 are dissolved in 10 ml of methylene chloride, and 0.2 ml of triethylamine and 0.2 ml of propionyl chloride are then added, with stirring. After 15 minutes, the reaction mixture is washed with water and then with 10% Na2CO3 solution and the organic phase is dried over MgSO4 and concentrated under vacuum. The residue is chromatographed on silica gel H using DCM and then a DCM/MeOH mixture (97/3; v/v) as the eluent. The product obtained is taken up with DCM, acidified to pH 1 by the addition of hydrochloric ether and concentrated under vacuum to give 0.52 g of the expected hydrochloride after crystallization from pentane. M.p.=115° C. (dec.). |
Here is a chemical reaction formula: Reactants are m4:CCCl, amount is: 0.0 MOLE;m1_m2_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5:Cl.Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CNC)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1, amount is: 0.0 ;m3:ClC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:C(Cl)Cl, amount is: 0.0 ;m6:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CN(C(=O)OCC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.41 ml of triethylamine is added to a solution of 0.5 g of the compound obtained in EXAMPLE 11, step B), in 10 ml of DCM, the mixture is then cooled to 0° C. and 0.14 ml of benzyl chloroformate is added dropwise. The reaction mixture is washed twice with water, dried over MgSO4 and concentrated under vacuum. The residue is chromatographed on silica gel H using DCM and then a DCM/MeOH mixture (94/6; v/v) as the eluent. The product obtained is taken up with DCM, acidified to pH 1 by the addition of hydrochloric ether and concentrated under vacuum to give 0.39 g of the expected hydrochloride after crystallization from iso ether. M.p.=135° C. |
Here is a chemical reaction formula: Reactants are m4:CCCl, amount is: 0.0 MOLE;m7_m1_m2_m3_m6:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C, amount is: 0.0 ;m7_m1_m2_m3_m6:Cl.Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CNC)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1, amount is: 0.0 ;m7_m1_m2_m3_m6:C1(=CC=CC=C1)CC(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 MOLE;m7_m1_m2_m3_m6:C(Cl)Cl, amount is: 0.0 ;m7_m1_m2_m3_m6:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O.Cl.C(C)(=O)NC1(CCN(CC1)CCOC(CN(C(=O)CC1=CC=CC=C1)C)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1.C(C)(=O)NC1(CCN(CC1)CCOC(CN(C)C(=O)CC1=CC=CC=C1)C1=CC(=C(C=C1)Cl)Cl)C1=CC=CC=C1.Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.46 ml of triethylamine and then 0.5 g of BOP are added to a mixture of 0.5 g of the compound obtained in EXAMPLE 11, step B), 0.127 g of phenylacetic acid and 10 ml of DCM. The resulting mixture is concentrated under vacuum and the residue is taken up with AcOEt, washed with water, with 1N NaOH solution and with saturated NaCl solution, dried over MgSO4 and concentrated under vacuum. The residue is chromatographed on silica gel H using DCM and then a DCM/MeOH mixture (94/6; v/v) as the eluent. The product obtained is taken up with DCM, acidified to pH 1 by the addition of hydrochloric ether and concentrated under vacuum to give 0.42 g of the expected hydrochloride after crystallization from iso ether. M.p.=125° C. |
Here is a chemical reaction formula: Reactants are m2:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ;m1:FC=1C(=NC(=NC1)CC1=CC=C(C=C1)F)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=NC(=NC=C1F)CC1=CC=C(C=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1.93 g (8.7 mmol) of 5-fluoro-2-(4-fluorobenzyl)-4-hydroxypyrimidine, from Step 1, and 15 mL of phosphorus oxychloride was heated in an oil bath at 90° C. for 1.5 hours and then concentrated in vacuo. The residue was triturated with 75 mL of ice water and the aqueous mixture was adjusted to pH 8-9 by the addition of solid sodium bicarbonate. The mixture was extracted with 3 X 70 mL of methylene chloride. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to a light brown residue. The residue was purified by flash chromatography on a 230-400 mesh silica gel column (4.8 X 14.6 cm) eluted with hexane:methylene chloride (1:1 v/v) to afford 1.94 g (90% yield) of the title compound; MS DCI-NH3M/Z: 241 (M+H)+ ; 1H NMR (CDCl3) d 4.22 (s, 2H), 7.00 (m, 2H), 7.30 (m, 2H), 8.48 (s, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=NC(=NC=C1F)CC1=CC=C(C=C1)F, amount is: 0.0 ;m1_m2_m3:CN1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C(=NC(=NC1)CC1=CC=C(C=C1)F)N1CCN(CC1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 0.48 g (2 mmol) of 4-chloro-5-fluoro-2-(4-fluorobenzyl)-pyrimidine from Step 2 and 1.53 mL (14 mmol) of 4-methylpiperazine in 10 mL of methylene chloride was stirred at ambient temperature for 1.5 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in methylene chloride. The resultant solution was washed with 4 X 30 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 0.59 g (95% yield) of the title compound as an oil; 1H NMR (CDCl3) d 2.32 (s, 3H), 2.47 (t, 4H), 3.78 (t, 4H), 3.99 (s, 2H), 6.97 (m, 2H), 7.29 (m, 2H), 7.97 (d, 1H). The product was carried on to the next step without purification. |
Here is a chemical reaction formula: Reactants are m5:C(=O)(OC(C)(C)C)N[C@@H](CCC)C(=O)NC1CNCC1, amount is: 0.0 MOLE;m4:ClC=1C=CN2C(C(=CC=C2C1)C(=O)OCC)=O, amount is: 0.0 MOLE;m3:ON1C(CCC1=O)=O, amount is: 0.0 MOLE;m1:NC1CN(CC1)CC1=CC=CC=C1, amount is: 0.0 MOLE;m2:C(C)(C)(C)OC(=O)N[C@@H](CCC)C(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N[C@@H](CCC)C(=O)NC1CN(CC1)C=1C=CN2C(C(=CC=C2C1)C(=O)O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3-Amino-1-benzylpyrrolidine (I. Sumio and T. Matsuo, Japanese Kokai JP 5328161, published Mar. 16, 1978) is coupled to N-t-butoxycarbonyl norvaline (Boc-nVal) using conventional N-hydroxysuccinimide coupling procedures. The 1-benzyl group is removed by hydrogenolysis in methanol using palladium on carbon catalyst. The 3-(N-Boc-norvalyl)aminopyrrolidine is then reacted with ethyl 8-chloro-4H-quinolizin-4-one-3-carboxylate, the product of Step 3 of Example 58, as described in Step 4 of Example 58, replacing 3-(N-t-butoxycarbonylamino)pyrrolidine with 3-(N-Boc-norvalyl)aminopyrrolidine, to give 8-(3-(N-norvalyl)amino-pyrrolidinyl)-4H-quinolizin-4-one-3-carboxylic acid with the nitrogen of the amino acid protected with a Boc group. The Boc protecting group is removed by standard hydrolysis using trifluoroacetic acid and dilute aqueous hydrochloric acid. |
Here is a chemical reaction formula: Reactants are m4_m2:[OH-].[Na+], amount is: 0.0 MOLE;m3:Cl, amount is: 0.0 ;m1:C(C)C=1C=C(C(N2C=CC(=CC12)N1CC(NCC1)C)=O)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(C)C=1C=C(C(N2C=CC(=CC12)N1CC(NCC1)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 0.686 g (2 mmol) of ethyl 1-ethyl-8-(3-methyl-1-piperazinyl)-4H-quinolizin-4-one-3-carboxylate, from Step 1, in 8 mL of THF was added 8.0 mL of a 1.0N aqueous sodium hydroxide solution and the reaction mixture was heated, with stirring, at 65° C. for 3 hours. The THF was removed from the reaction mixture by distillation during the reaction. The concentrated reaction mixture was cooled to ambient temperature and adjusted to pH 1-2 with 16 mL of 1N aqueous hydrochloric acid solution. The aqueous solution was concentrated in vacuo to remove the water and the residue was suspended in 10 mL of water. The solid was collected by filtration and dried in vacuo to afford the 385 mg (55% yield) of the title compound, m.p.>295° C.; MS DCI-NH3 : 316 (M-Cl)+ ; IR (KBr): 3420 (OH), 1720 (C=O) cm-1 ; 1H NMR (TFA) d 1.50 (t, 3H, J=7.5 Hz), 1.70 (d, 3H, J=6 Hz), 3.00 (q, 2H, J=7.5 Hz), 3.70-4.10 (m, 6H), 4.55 (m, 1H), 4.60 (m, 1H), 7.40 (d, 1H, J=3.0 Hz), 7.68 (dd, 1H, J=3.0 Hz, 8.4 Hz), 8.18 (s, 1H), 9.19 (d, 1H, J=8.4 Hz). Analysis calculated for C17H22 ClN3O3 +H2O: C, 55.21; H, 6.54; N, 11.36. Found: C, 55.19; H, 6.07; N, 11.34. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 ;m1_m4_m2:C(C)C=1C=C(C(N2C=CC(=CC12)N1CCN(CC1)C)=O)C(=O)OCC, amount is: 0.0 ;m1_m4_m2:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(C)C=1C=C(C(N2C=CC(=CC12)N1CCN(CC1)C)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 171 mg (0.5 mmol) of ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-4H-quinolizin-4-one-3-carboxylate, from Step 1, in 4 mL of THF was added 4.0 mL of a 1.0N aqueous sodium hydroxide solution and the reaction mixture was heated, with stirring, at 75° C. for 4.5 hours. The reaction mixture was cooled to ambient temperature and adjusted to pH 2 with 5 mL of 1N aqueous hydrochloric acid solution. The aqueous solution was concentrated in vacuo to ~5 mL and the solid was collected by filtration and dried in vacuo to afford 120 mg (68% yield) of the title compound, m.p. 293°-294° C. (dec); MS DCI-NH3 : 316 (M-Cl)+ 90%, 272 ((M-Cl)--CO2H)+ base; IR (KBr): 3420 (OH), 1695 (C=O), 1640 (C=O) cm-1 ; 1H NMR (TFA) d 1.47 (t, 3H, J=7.5 Hz), 3.00 (q, 2H, J=7.5 Hz), 3.23 (s, 3H), 3.55 (dd, 2H, J=9 Hz), 4.12 (m, 4H), 4.65 (d, 2H, J=15 Hz), 7.40 (s, 1H), 7.67 (d, 1H, J=9 Hz), 8.18 (s, 1H), 9.20 (d, 1H, J=7.5 Hz). Analysis calculated for C17H22ClN3O3 : C, 56.59; H, 6.42; N, 11.64. Found: C, 56.86; H, 6.19; N, 11.60. |
Here is a chemical reaction formula: Reactants are m2_m3:FC1=CC=C([N+](=C1)[O-])C, amount is: 0.0 MOLE;m2_m3:FC1=CC=C([N+](=C1)[O-])C, amount is: 0.0 ;m1:[OH-].[Na+], amount is: 0.0 MOLE;m5:[N+](=O)([O-])[O-].[K+], amount is: 0.0 ;m4:S(O)(O)(=O)=O, amount is: 0.0 ;m6:[N+](=O)([O-])[O-].[K+], amount is: 0.0 MOLE;m7:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC1=C(C=C([N+](=C1)[O-])C)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The reaction was carried out in a flask vented to a gas scrubber containing aqueous sodium hydroxide solution. The product of Step 5, 5-fluoro-2-picoline-N-oxide (1.0 g, 7.86 mmol) was cooled to 0° C. and concentrated sulfuric acid (4.2 mL) was slowly added, with stirring. Solid potassium nitrate (1.27 g, 12.5 mmol) was then added to this mixture at 0° C., in small portions over a 45 minute period. The reaction mixture was allowed to warm to ambient temperage and was stirred at ambient temperature for 1 hour. Not all of the potassium nitrate had dissolved and the reaction mixture was heated at 50° C. for 0.5 hours and then at 100° C. for 18 hours. The homogeneous reaction solution was poured over ice and the resultant aqueous solution was adjusted to pH 9 with solid potassium carbonate. The aqueous solution was then extracted with 3 X 80 mL of methylene chloride. The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1.084 g (80% yield) of the title compound as a yellow solid, m.p. 107°-108° C.; MS DCI-NH3M/Z: 190 (M+NH4)+ 10%, 173 (M+H)+ 30%, 157 (M-O)+ 50%; 1H NMR (CDCl3) d 2.48 (s, 3H), 8.05 (d, 1H, J=9.0 Hz), 8.31 (d, 1H, J=6.0 Hz). |
Here is a chemical reaction formula: Reactants are m2:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m1_m3:ClC=1C=C([N+](=CC1F)[O-])C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)(=O)O, amount is: 0.0 ,Catalysts are m4:[Fe], amount is: 0.0 .Products are 0:ClC1=CC(=NC=C1F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Chloro-5-fluoro-2-picoline-N-oxide (12.43 g, 76.93 mmol), from Step 7, was dissolved in 52 mL of glacial acetic acid in a 3-necked flask equiped with a mechanical stirrer, a condenser and a thermometer. Iron powder (6.45 g, 115.5 mmol) was added to the solution at ambient temperature and the reaction mixture was carefully heated to 35°-40° C. After 10 min at 30° C., an exothermic reaction took place which caused the reaction temperature to rise to 120° C. and the reaction mixture became a very dark brown-colored solution. The flask was transferred to a cold water bath and the temperature of the solution brought down to ambient. The reaction mixture was then poured over ice. The resultant aqueous mixture was adjusted to pH 9 with potassium carbonate and steam distilled. The aqueous distillate collected at 92°-96° C. was extracted with three portions of methylene chloride. The combined organic extract was dried over anhydrous sodium sulfate, filtered and distilled to afford 15.91 g (71% yield) of the title compound, b.p. 138°-140° C.; MS GC-MS M/Z: 146 (M+H)+ ; 1H NMR (CDCl3) d 2.53 (s, 3H), 7.23 (d, 1H, J=6.0 Hz), 8.37 (s, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m5:ClC1=CC(=NC=C1F)C, amount is: 0.0 ;m1_m2_m5:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE;m4:O, amount is: 0.0 MOLE;m3:C(C)(C)(C)OCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:C(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C(=NC=C(C1Cl)F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 0.87 g (6 mmol) of 4-chloro-5-fluoro-2-picoline, the product of Example 66, in 20 mL of chloroform cooled to -45° C., is added 0.75 mL of t-butylhypochlorite. The reaction mixture is stirred at -45° C. for 2 hours and at 0° C. for 2 hours. The reaction mixture is then poured into water and the resultant aqueous mixture is extracted with methylene chloride. The organic solution is dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and distilled to afford the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE;m1_m2_m3:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE;m1_m2_m3:BrBr, amount is: 0.0 MOLE;m4:S(O)(O)(=O)=O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:BrC=1C(=NC=C(C1Cl)F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Chloro-5-fluoro-2-picoline, the product of Example 66, is treated with bromine in fuming sulfuric acid containing 65% sulfur trioxide for 7 hours at 80° C. as described by L. van der Does and H. J. Hertog in Rec Trav Chim 81: 864 (1965) to afford the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE;m1_m2:FOC(C)=O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=C(C(=NC=C1F)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Chloro-5-fluoro-2-picoline is treated with 1.1 equivalents of acetyl hypofluorite as described by O. Lerman, et al. J Org Chem, 49: 806-813 (1984) to afford the title compound. |
Here is a chemical reaction formula: Reactants are m3:ClC1=CC(=NC=C1F)CCC, amount is: 0.0 MOLE;m1:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE;m4:ClC1=CC(=NC=C1F)CCC, amount is: 0.0 MOLE;m2:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C(=NC=C(C1Cl)F)CCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: By following the procedures described in Example 67 and replacing 4-chloro-5-fluoro-2-picoline (the product of Example 66) with 4-chloro-5-fluoro-2-propyl-pyridine (the product of Example 70), the title compound can be prepared. |
Here is a chemical reaction formula: Reactants are m3:ClC1=CC(=NC=C1F)CCC, amount is: 0.0 MOLE;m2:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE;m1:ClC1=CC(=NC=C1F)C, amount is: 0.0 MOLE;m4:ClC1=CC(=NC=C1F)CCC, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC1=C(C(=NC=C1F)CCC)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: By following the procedures described in Example 69 and replacing 4-chloro-5-fluoro-2-picoline (the product of Example 66) with 4-chloro-5-fluoro-2-propyl-pyridine (the product of Example 70), the title compound can be prepared. |
Here is a chemical reaction formula: Reactants are m1_m3:ClC1=CC(NC=C1F)(C)Br, amount is: 0.0 ;m2:CN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC(=NC=C1F)CNC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Chloro-5-fluoro-alpha-bromo-2-picoline (1.37 g, 6.1 mmol), from Step 1 was dissolved in 15 mL of methanol in a pressure tube. Methylamine (3 mL of 40% aqueous solution) was added to the tube and the tube was sealed. The reaction mixture was stirred at ambient temperature for 26 hours and then the solvent was removed under reduced pressure. To the residue was added 50 mL of 10% aqueous sodium carbonate solution and the resultant aqueous mixture was extracted with 3 X 50 mL of methylene chloride. The organic combined extract was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressur. The residue was dried in vacuo to give 754 mg g (70% yield) of the title compound; MS DCI-NH3M/Z: 175 (M+H)+ base; 1H NMR (CDCl3) d 2.50 (s, 3H), 3.90 (s, 2H), 7.47 (d, 1H), 8.42 (s, 1H). |
Here is a chemical reaction formula: Reactants are m1_m4_m2:C(C)C=1C=C(C(N2C(=C(C(=C(C12)F)N1CCN(CC1)C)F)F)=O)C(=O)OCC, amount is: 0.0 ;m1_m4_m2:[OH-].[Na+], amount is: 0.0 MOLE;m3:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(C)C=1C=C(C(N2C(=C(C(=C(C12)F)N1CCN(CC1)C)F)F)=O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 199 mg (0.5 mmol) of ethyl 1-ethyl-8-(4-methylpiperazin-1-yl)-6,7,9-trifluoro-4H-quinolizin-4-one-3-carboxylate, from Step 5, in 4 mL of THF is added 4.0 mL of a 1.0N aqueous sodium hydroxide solution and the reaction mixture is heated, with stirring, at 75° C. for 4.5 hours. The reaction mixture is cooled to ambient temperature and adjusted to pH 2 with 5 mL of 1N aqueous hydrochloric acid solution. The aqueous solution is concentrated in vacuo to ~5 mL and the solid is collected by filtration and dried in vacuo to afford the title compound. |
Here is a chemical reaction formula: Reactants are m1_m4:ClC1=C(C(=NC=C1F)C(COC1OCCCC1)C)F, amount is: 0.0 MOLE;m2_m3:O, amount is: 0.0 MOLE;m2_m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C(=NC=C1F)C(CO)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The product of Step 1 is dissolved in 200 mL of 2:1 THF:water and to this solution is added 6 mL of acetic acid. The reaction mixture is heated at 45° C. for approximately 5 hours. The THF is removed under reduced pressure and the aqueous reaction mixture is adjusted to a pH in the range of 8 to 9 with 10% sodium carbonate and is then extracted with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound. |
Here is a chemical reaction formula: Reactants are m1_m6:C(C)(C)(C)OC1=C(C(=NC(=C1)F)F)F, amount is: 0.0 MOLE;m4_m5:OO, amount is: 0.0 ;m4_m5:[OH-].[Na+], amount is: 0.0 ;m3:COB(OC)OC, amount is: 0.0 ;m2:[Li+].CC(C)[N-]C(C)C, amount is: 65.5999984741211 MILLIMOLE,this reaction does not need reagents,Solvents are m1_m6:C1CCOC1, amount is: 0.0 ;m7:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC1=C(C(=NC(=C1O)F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 11.16 g (54.39 mmol) sample of 4-t-butoxy-2,3,6-trifluoropyridine, from Example 253 step b above, was dissolved in 50 mL of THF, and the solution was cooled to -78° C. To this solution was added LDA (65.6 mmol) with stirring for 30 min, during which a solid preciptated. To this mixture was added 7.5 mL of trimethoxyborane, with stirring for 25 min at -78° C. To this mixture was added 10 mL of acetic acid, and the mixture was stirred and allowed to warm to room temperature. Next was added 100 mL of 30% hydrogen peroxide and 100 mL of 2N sodium hydroxide while cooling in an ice bath. The mixture was then stirred at room temperature for 16 hours, and quenched with saturated NH4Cl solution. The mixture was extracted with ether, and the extract was washed with brine and dried over MgSO4. The solvent was removed under vacuum, and the residue was purified by flash chromatography on silica gel, eluting with 1:8 ethyl acetate:hexane. Removal of the solvent gave 9.769 g of the title product as a colorless liquid. |
Here is a chemical reaction formula: Reactants are m4:CCOC(=O)/N=N/C(=O)OCC, amount is: 0.0 ;m1_m5_m2_m3:C(C)(C)(C)OC1=C(C(=NC(=C1O)F)F)F, amount is: 0.0 ;m1_m5_m2_m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m5_m2_m3:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC1=C(C(=NC(=C1OC)F)F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 237 mg (1.07 mmol) of 4-t-butoxy-2,3,6-trifluoro-5-hydroxypyridine, from step 275a above, in 3 mL of anhydrous THF was added 335 mg (1.277 mmol) of triphenyl phosphine and 0.060 mL (1.48 mmol) of methanol. To this solution was added 0.200 mL (1.270 mmol) of DEAD dropwise at room temperature. The reaction was complete in 10 min, so the solvents were removed under vacuum and the residue was purified by flash chromatography on silica gel, eluting with 1:16 ethyl acetate:hexane to give 215.6 mg of the title product as a colorless liquid after removal of the solvent. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE;m2:C(C)(C)(C)OC(=O)N[C@@H](C)[C@H]1CNCC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(C)#N, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:Cl.N[C@@H](C)[C@H]1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in anhydrous acetonitrile, reacted with (3R,1S)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine (prepared as described by Schroeder et al., J. Heterocyclic Chem., 29:1481-1498 (1992)), and carried forward as described in Example 253k-l to give the title product. mp 250°-255° C. (dec.). MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.59 (m, 2H), 1.00 (m, 2H), 1.29 (d, 3H, J=6 Hz), 1.77 (m, 1H), 2.13 (m, 1H), 2.29 (m, 1H), 2.41 (m, 1H), 2.64 (s, 3H), 3.57 (s, 1H), 3.76 (m, 3H), 3.94 (m, 1H), 7.91 (s, 1H), 8.17 (brs, 3H), 9.07 (d, 1H, J=11 Hz), 13.83 (brs, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE;m1_m2_m4:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m3:C(C)(C)(C)OC(=O)N[C@H](C)[C@@H]1CNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.N[C@H](C)[C@@H]1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 0.44 g sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, and 1.51 g of NaHCO3 were dissolved in 40 mL of anhydrous acetonitrile, reacted with (3S,1R)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidine (1.06 g, prepared as described by Schroeder et al., J. Heterocyclic Chem., 29:1481-1498 (1992)), and carried forward as described in Example 253k-l to give the title product. mp 235°-240° C. (dec.). MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.59 (m, 2H), 1.00 (m, 2H), 1.29 (d, 3H, J=6 Hz), 1.76 (m, 1H), 2.13 (m, 1H), 2.28 (m, 1H), 2.41 (m, 1H), 2.63 (s, 3H), 3.30 (m, 1H), 3.74 (m, 3H), 3.94 (m, 1H), 7.90 (s, 1H), 8.16 (br s, 3H), 9.07 (d, 1H, J=11 Hz). |
Here is a chemical reaction formula: Reactants are m3:C(C)(C)(C)OC(=O)N[C@H](C)[C@H]1CNCC1, amount is: 0.0 ;m1_m2_m4:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE;m1_m2_m4:C([O-])(O)=O.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.NC(C)C1CN(CC1)C=1C(=C2C(=CC(=CN2C(C1C(=O)O)=O)F)C)C1CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 0.35 g sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, and 0.73 g of sodium bicarbonate were dissolved in 24 mL of anhydrous acetonitrile, reacted with (3R,1R)-3-(1-(t-butoxycarbonylamino)ethyl)-pyrrolidine (0.51 g, prepared as described by Schroeder et al., J. Heterocyclic Chem., 29:1481-1498 (1992)), and carried forward as described in Example 253k-l to give the title product. mp 220°-222° C. MS 374 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.61 (m, 2H), 0.94 (m, 1H), 1.07 (m, 1H), 1.28 (d, 3H, J=6 Hz), 1.82 (m, 1H), 2.27 (m, 2H), 2.46 (m, 1H), 2.62 (s, 3H), 3.57 (s, 1H), 3.92 (m, 1H), 7.90 (s, 1H), 8.17 (br s, 3H), 9.07 (d, 1H, J=l 1 Hz), 13.84 (brs, 1H). |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE;m2:N1(CCCCC1)C1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCCCC1)C1CCN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 70 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 4-(1-piperidyl)piperidine (70 mg, 0.4 mmol, Aldrich Chem. Co.), and carried forward as described in Example 253j-k to give the title product. MS 428 (M+H)+ ; 1H NMR (CDCl3) ∂: 0.69 (m, 2H), 1.02 (m, 2H), 1.18 (m, 4H), 2.27 (n, 1H), 2.78 (s, 3H), 2.72 (m, 1H), 3.35 (m, 3H), 3.55 (m, 1H), 3.75 (m, 1H), 8.36 (s, 1H), 9.20 (d, 1H). Anal. Calcd for C24H30 N3O3F.1.5 H2O: C, 63.42; H, 7.32; N, 9.24; Found: C, 62.99; H, 7.04; N, 8.78. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE;m2:N1=C(C=CC=C1)N1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=C(C=CC=C1)N1CCN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 60 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 4-(2-pyridyl)piperazine (63.5 mg, 0.39 mmol, Aldrich Chem. Co.), and carried forward as described in Example 253j-k to give the title product. MS 423 (M+H)+ ; 1H NMR (CDCl3) ∂: 0.71 (m, 2H), 1.05 (m, 2H), 2.30 (m, 1H), 2.86 (s, 3H), 3.59 (m, 4H), 3.78 (m, 4H), 6.76 (m, 2H), 7.57 (m, 1H), 8.25 (m, 1H), 8.40 (s, 1H), 8.25 (d, 1H), 13.83 (bs, 1H). Anal. Calcd for C23H23N4O3F.1.5 H2O: C, 61.46; H, 5.83; N, 12.46; Found: C, 61.76; H, 5.54; N, 11.64. |
Here is a chemical reaction formula: Reactants are m2:N1CCCC1, amount is: 0.0 MOLE;m1_m3:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.NC(C)(C)C1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 150 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 2 mL of anhydrous acetonitrile, reacted with 1-amino-1-methylethyl)pyrrolidine (155 mg, 0.77 mmol, prepared by standard method from the free base described by Hayakawa et al., U.S. Pat. No. 5,098,912, issued Mar. 24, 1992), and carried forward as described in Example 253k-l to give the title product. MS (high resolution) found: 388.2047; calc: 388.2036 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.60 (m, 2H), 0.94 (m, 1H), 1.07 (m, 1H), 1.33 (s, 3H), 1.34 (s, 1H), 2.83 (m, 1H), 2.07 (m, 1H), 2.19 (m, 2H), 2.63 (s, 3H), 3.60 (b t, 1H), 3.68 (b t, 1H), 3.81 (m, 1H), 3.93 (m, 1H), 7.90 (s, 1H), 8.11 (b s, 1H), 9.08 (d, 1H), 13.83 ( b s, 1H). Anal. Calcd for C21H27N3O3FCl.1.5 H2O: C, 55.93; H, 6.71; N, 9.32; Found: C, 56.07; H, 6.71; N, 8.95. |
Here is a chemical reaction formula: Reactants are m2:C(=O)(OC(C)(C)C)NC(CCC)C1CNCC1, amount is: 0.0 ;m1_m3:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.NC(CCC)C1CN(CC1)C=1C(=CN2C(C(=CC(=C2C1C)C1CC1)C(=O)O)=O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 238 mg sample of 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester, from Example 253i above, was dissolved in 5 mL of anhydrous acetonitrile, reacted with 3-(1-(N-BOC-amino)butyl)pyrrolidine (620 mg, 1.83 mmol, prepared in step 314d above), and carried forward as described in Example 253j-1 to give the title product. MS (high resolution) found: 402.2199; calc: 402.2193 (M+H)+ ; 1H NMR (D6 -DMSO) ∂: 0.60 (m, 2H), 0.89 (m, 4H), 1.05 (m, 1H), 1.49 (m, 5H), 1.17 (m, 1H), 2.14 (m, 1H), 2.27 (m, 1H), 2.62 (s, 3H), 3.77 (m, 4H), 3.94 (m, 1H), 7.89 (s, 1H), 8.54 (b m, 1H), 9.07 (d, 1H), 11.47 (br, 1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)N1CC(CC1)NC(C(F)(F)F)=O, amount is: 0.0 MOLE;m1_m2_m3:[H-].[H-].[H-].[H-].[Li+].[Al+3], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)NCC(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 2.64 g sample of the compound from step 447a was added dropwise to a suspension of 1.11 g of LAH in ether stirred under N2 at 0° C. After one hour, the reaction was stirred at room temperature for 6 hours. The reaction was quenched by sequential addition of 1.2 mL of water, 1.2 mL of 15% NaOH and 2.4 mL of water. The mixture was filtered, and the filtrate was concentrated to give 2.39 of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)N1CC(CC1)N(CCF)C(=O)OC(C)(C)C, amount is: 0.0 MOLE;m1_m2_m3:C(=O)[O-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 MOLE.Products are 0:C(=O)(OC(C)(C)C)N(CCF)C1CNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 225 mg sample of the compound from step 448a was treated with ammonium formate and 10% Pd/C according to the procedure of step 445b for 1 hour, and the title compound was isolated (190 mg). |
Here is a chemical reaction formula: Reactants are m3:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m4:FC(C(C(=O)O)=C)(F)F, amount is: 0.0 MOLE;m2_m5:C(C1=CC=CC=C1)N(COC)C[Si](C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ;m2_m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 2.48 g sample of 2-(trifluoromethyl)acrylic acid was dissolved in 40 mL of dry methylene chloride, and a solution of 4.75 g of N-benzyl-N-(methoxymethyl)-trimethylsilylmethylamine in 20 mL of dry methylene chloride was added dropwise under N2 at 0° C. To this mixture was added 2 mL of trifluoroacetic acid, and the mixture was stirred for 2 hours at room temperature. The product was removed by filtration, washed and dried to give the title product. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F, amount is: 0.0 ;m1_m2_m4_m3:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-], amount is: 0.0 ;m1_m2_m4_m3:CN(C)C, amount is: 0.0 ;m1_m2_m4_m3:C(C)(C)(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)(C(F)(F)F)NC(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1.42 g of the compound from step 454a, 1.71 g of diphenylphosphoryl azide, 12.3 g of t-butanol and 0.627 g of trimethyl amine was heated at reflux under N2 for 24 hours. The mixture was concentrated to dryness, and the residue was dissolved in methylene chloride. The solution was washed with satd. NaHCO3 and water, then concentrated. The residue was chromatographed on silica gel to give 1.73 g of the title compound. |
Here is a chemical reaction formula: Reactants are m2_m5:C(C1=CC=CC=C1)N(COC)C[Si](C)(C)C, amount is: 0.0 ;m1_m4:FC(C(C(=O)O)=C)(F)F, amount is: 0.0 ;m3:C(=O)(C(F)(F)F)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C(Cl)Cl, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(Trifluoromethyl)acrylic acid (2.48 g, 20 mmol) was dissolved in 30 mL of dry methylene chloride, a solution of 4.75 g (20 mmol) of N-benzyl-N-(methoxymethyl)-trimethylsilylmethylamine in 20 mL of dry methylene chloride was added dropwise under N2 at 0° C. To this solution was added 2 mL of TFA, and the solution was stirred for 2 hours at room temperature. The white precipitate was collected, washed and dried to give 3.22 g of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C1=CC=CC=C1)N1CC(CC1)(C(=O)O)C(F)(F)F, amount is: 0.0 ;m2:[H-].[H-].[H-].[H-].[Li+].[Al+3], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)(CO)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The compound from step 456a (2.32 g) was dissolved in 60 mL of dry THF, 1.12 eq of LAH (1N in dry THF) was added, and the reaction was stirred under N2 for 3 hours. The reaction was quenched by the sequential dropwise addition of 0.35 mL water, 0.35 mL of 15% NaOH and 1.3 mL of water, then the mixture was stirred for 1 hour and filtered. The filtrate was dried and concentrated to give 2.2 g of the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1_m2_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m4:C(C1=CC=CC=C1)N1CC2C(NC(CC2C1)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC2C(N(C(CC2C1)=O)CC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 905 mg of K2CO3 and 400 mg of the compound from step 457b in 5 mL of DMF was added 308 mg of benzyl bromide, and the reaction mixture was stirred at room temperature under N2 for 6.5 hours. The mixture was diluted with ethyl acetate, which was washed with water and brine, dried and concentrated to give 610 mg of the title compound. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)N1C(C2C(CC1=O)CNC2)=O, amount is: 0.0 ;m1_m3:[H-].[H-].[H-].[H-].[Li+].[Al+3], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C(Cl)Cl, amount is: 0.0 ;m1_m3:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC2C(CC1)CNC2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 266 mg of LAH in 10 mL of ether was stirred at 10° C. under N2. To this suspension was added 540 mg of the compound from step 457d dissolved in 10 mL of methylene chloride. The mixture was stirred under N2 for 1.5 hours. The reaction was quenched by the sequential dropwise addition of 0.3 mL water, 0.3 mL of 15% NaOH and 0.6 mL of water, then the mixture was stirred for 1 hour and filtered. The filtrate was dried and concentrated to give 389 mg of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C1=CC=CC=C1)N1CC(CC1)C(=O)C1CC1, amount is: 0.0 MOLE;m1_m2_m3_m4:C(C)(=O)[O-].[NH4+], amount is: 0.0 ;m1_m2_m3_m4:[BH3-]C#N.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)C(C1CC1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A 1 g sample of the compound from step 470b, 3.37 g of ammonium acetate and 274 mg of NaBH3CN were dissolved in 15 mL of methanol, 1.2 g of 4 Å molecular sieves were added, and the mixture was stirred at room temperature under N2 for 16 hours. The mixture was filtered, the sieves washed with methanol, the wash and filtrate combined, and concentrated. The residue was dissolved in 100 mL of methylene chloride, and 30 mL of 15% NaOH was added. The organic phase and a second wash of the aqueous phase were combined and washed with water and brine, then dried over MgSO4. The solvent was removed, and the residue was chromatographed on silica gel to give 460 mg of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2:C(=O)(OC(C)(C)C)NC(C1CC1)C1CN(CC1)CC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:CO, amount is: 0.0 MOLE,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:C(=O)(OC(C)(C)C)NC(C1CC1)C1CNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A sample (548 mg) of the compound from step 470d was dissolved in methanol, 140 mg of 10% Pd/C was added, and the mixture was hydrogenated at 4 atm H2 for 42 hours at room temperature. The solution was filtered, and the solvent was removed to give 140 mg of the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)Cl)C)C1CC1, amount is: 0.0 MOLE;m1_m5:[H-].[Na+], amount is: 0.0 MOLE;m2:C(CC(=O)OC(C)(C)C)(=O)OC(C)(C)C, amount is: 0.0 MOLE;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)OC(=O)C1=CC(=C2C(=C(C(=CN2C1=O)F)CC(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1)C)C1CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of NaH in DMF with ice bath cooling is added di-t-butyl malonate. After the addition, 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester from Example 253i above is added. The reaction is then heated to 50° to 60° C., and the mixture is poured into water and acidified. The product is extracted into methylene chloride and dried over MgSO4. The residue, after removal of the solvent, is dissolved in methylene chloride and trifluoroacetic acid at room temperature. The solvent is removed under vacuum, and the product is treated with diphenyldiazomethane in methylene chloride and methanol. When the reaction is finished, the solvents are removed under vacuum, and the product is purified by column chromatography to give the title compound. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)#N, amount is: 0.0 ;m5_m1:CN(C=O)C, amount is: 0.0 ;m3:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:O, amount is: 0.0 ,Catalysts are m5_m1:[Cl-].[Zn+2].[Cl-], amount is: 0.0 ;m6:[Cl-].[Zn+2].[Cl-], amount is: 0.0 MOLE.Products are 0:C1(=CC=CC=C1)C1=NN=NN1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Zinc chloride (3.3 g, 24.3 mmol, 0.5 eq) was added to 15 mL of N,N-dimethylformamide in small portions while maintaining the temperature below 60° C. The suspension of zinc chloride was cooled to room temperature and treated with 5.0 g of benzonitrile (48.5 mmol, 1.0 eq) followed by 3.2 g of sodium azide (48.5 mmol, 1.0 eq). The heterogeneous mixture was heated at 115° C. with agitation for 18 hours. The mixture was cooled to room temperature, water (30 mL) was added and the mixture acidified by the addition of 5.1 mL of concentrated hydrochloric acid. The mixture was cooled to 0° C. and aged for one hour, then filtered and the filter cake washed with 15 mL of cold 0.1N HCl then dried at 60° C. under vacuum to afford 6.38 g (43.7 mmol, 90%) of the product. |
Here is a chemical reaction formula: Reactants are m3_m6:C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl, amount is: 0.0 ;m4:O, amount is: 0.0 ;m2:C(C)N(CC)CC, amount is: 0.0 ;m1_m5:C1(=CC=CC=C1)C1=NN=NN1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m6:O1CCCC1, amount is: 0.0 ;m1_m5:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)C=1N=NN(N1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 5.0 g (34.2 mmol) of 5-phenyltetrazole in 55 mL of acetone was added 5.0 mL of triethylamine (3.6 g, 35.6 mmol, 1.04 eq). After 15 minutes, a solution of 10.0 g of triphenylmethyl chloride (35.9 mmol, 1.05 eq) in 20 mL of tetrahydrofuran was added and the mixture stirred at room temperature for one hour. Water (75 mL) was slowly added and the mixture stirred for one hour at room temperature. The product was collected by filtration, washed with 75 mL of water and dried at 60° C. under vacuum to give 13.3 g (34.2 mmol, 100%) of the product. |
Here is a chemical reaction formula: Reactants are m3:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-], amount is: 0.0 ;m4:C(C1=CC=CC=C1)O, amount is: 0.0 ;m1_m5_m2:COC(CC(C(=O)O)(C)C)=O, amount is: 0.0 ;m1_m5_m2:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC(CC(=O)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 14.7 g (91.8 mmol) of 2,2-dimethylbutanedioic acid-4-methyl ester in 150 mL of benzene was added 13 mL of triethylamine (9.4 g, 93 mmol) followed by 21.8 mL of diphenylphosphoryl azide (27.8 g, 101 mmol). The mixture was heated under nitrogen at reflux for 45 minutes then 19 mL (19.9 g, 184 mmol) of benzyl alcohol was added and refluxing continued for 16 hours. The mixture was cooled, filtered and the filtrate concentrated to a minimum volume under vacuum. The residue was redissolved in 250 mL of ethyl acetate, washed with water, saturated aqueous sodium bicarbonate (2×) and brine. The organic layer was removed, dried over magnesium sulfate, filtered and the filtrate concentrated to a minimum volume under vacuum. The crude product was purified by medium pressure liquid chromatography on silica, eluting with hexane/ethyl acetate (4:1), to afford 18.27 g (68.9 mmol, 75%) of the product. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC(CC(C)(C)NC(=O)OCC1=CC=CC=C1)=O, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC(CC(=O)O)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 18.27 g (68.9 mmol) of 3-benzyloxycarbonylamino-3-methylbutanoic acid methyl ester in 20 mL of methanol at room temperature was treated dropwise with 51 mL of 2N NaOH (102 mmol). The mixture was stirred at room temperature for 16 hours then transferred to a separatory funnel and washed with hexane (3×). The aqueous layer was removed, cooled to 0° C. and slowly acidified to pH 2 (paper) by dropwise addition of 6N HCl. This mixture was extracted with ether (6×); combined extracts were washed with 1N HCl and brine, then dried over magnesium sulfate, filtered and solvent removed under vacuum to afford 17.26 g (68.7 mmol, 99%) of the product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)OCC1=CC=CC=C1)CC1=CNC2=CC=CC=C12)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:C(C)(C)(C)OC(=O)NC(C(=O)N[C@@H](C(=O)O)CC1=CNC2=CC=CC=C12)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The benzyl ester (0.82 g, 1.71 mmol) obtained in Step C and 10% palladium on carbon (150 mg) were stirred together in ethyl acetate (5 mL). The solution was degassed and a hydrogen atmosphere introduced over the reactants using a balloon for 32 hours. The reaction products were isolated by filtering the reaction mixture through a Celite plug. The plug was washed with additional ethyl acetate (3×10 mL). The combined filtrates were evaporated under vacuum to afford the product (680 mg, 102%). 1H NMR (400 MHz, CDCl3): 1.30 (s, 9H), 1.41 (s, 6H), 3.32 (dd, 1H), 3.42 (m, 1H), 4.87 (br s, 1H), 6.82 (d, 1H), 7.13-7.35 (m, 8H), 7.60 (d, 1H), 8.28 (br s, 1H). |
Here is a chemical reaction formula: Reactants are m3:C(=O)(OCC1=CC=CC=C1)NC(C)(C(=O)O)C, amount is: 0.0 ;m1:C(C=C)OC([C@H](N)CCC1=CC=CC=C1)=O, amount is: 0.0 MOLE;m4:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C, amount is: 0.0 ;m2:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C=C)OC([C@@H](CCC1=CC=CC=C1)NC(C(C)(C)NC(=O)OCC1=CC=CC=C1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The amine obtained in Step B of this Example (300 mg; 1.37 mmol) triethylamine (380 ml; 2.73 mmol) and N-carbobenzyloxy-2-methylalanine (278 mg; 1.37 mmol) were dissolved in dry methylene chloride (3 ml) and BOP (605 mg; 1.37 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and the resultant homogenous yellow solution quenched by addition of brine. The two phase system was extracted with methylene chloride (2×25 ml) and the combined methylene chloride layers dried over powdered anhydrous magnesium sulfate. Filtration of the methylene chloride solution to remove the spent drying agent followed by evaporation of solvent afforded an oil which was purified by column chromatography on silica gel using a solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant. The desired product (419 mg; 69.7%) was isolated as a white amorphous solid. FAB-MS:- calculated for C25 H30N2O5 438.2; found 439.3 (M+1). |
Here is a chemical reaction formula: Reactants are m4:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C, amount is: 0.0 MOLE;m1_m2_m3_m5:C(C=C)OC([C@H](N)CCC1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m3_m5:C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(Cl)Cl, amount is: 0.0 ;m8:C(C)(=O)OCC, amount is: 0.0 MOLE;m7:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C=C)OC([C@@H](CCC1=CC=CC=C1)NC(CC(C)(C)NC(=O)OCC1=CC=CC=C1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: D-Homophenylalanine allyl ester (350 mg; 1.60 mmol), triethylamine (445 μl; 3.19 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (412.8 mg; 1.64 mmol) were dissolved in dry methylene chloride (3 ml) and stirred at room temperature to give a homogeneous solution. BOP was added to the solution over 5 minutes and the reaction mixture stirred together at room temperature for 12 h. The reaction mixture was quenched by adding brine (10 ml) directly to the reaction. The crude products were isolated by extraction with methylene chloride (2×25 ml); the combined methylene chloride extracts dried with powdered anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The pale yellow oil thus obtained was subjected to column chromatography on silica gel using an eluant of ethyl acetate and hexanes (1:1 v/v). In this way, 432 mg (59.7%) of the desired product was isolated as a colorless oil. FAB-MS: -calculated for C26H32N2O5 452.2; found 453.4 (M+1). |
Here is a chemical reaction formula: Reactants are m1_m4:C(C)(C)(C)OC(=O)N[C@H](CC1=CNC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m3:C(C=C)Br, amount is: 0.0 ;m2:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CC(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C=C)OC([C@H](NC(=O)OC(C)(C)C)CC1=CNC2=CC=CC=C12)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-(t-Butoxycarbonyl)-D-tryptophan (3 g; 9.868 mmol) was dissolved in acetone and an aqueous solution of potassium carbonate (2.84 g; 20.58 mmol) added followed by allyl bromide (1.55 g; 12.81 mmol). The reaction mixture was stirred for 18 h and then the acetone was substantially removed by evaporation under reduced pressure. The oily water layer that remained was acidified to approximately pH=5 with 1N-hydrochloric acid and then extracted with methylene chloride. The methylene chloride layer was dried over anhydrous magnesium sulfate powder, filtered and evaporated under reduced pressure to give a foamy solid. The foam was further purified by column chromatography using silica gel and ethyl acetate and hexanes 2:1 v/v as eluant. In this manner, a 1.92 g yield (56%) of the desired product was obtained as an off white solid. FAB-MS:- calculated for C19H24N2O4 344; found 344 (M). |
Here is a chemical reaction formula: Reactants are m4:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C, amount is: 0.0 ;m1_m2_m3_m5:C(C=C)OC([C@H](N)CC1=CNC2=CC=CC=C12)=O, amount is: 0.0 ;m1_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m3_m5:C(C1=CC=CC=C1)OC(=O)NC(C)(C(=O)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(Cl)Cl, amount is: 0.0 ;m7:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC(C(=O)N[C@@H](C(=O)OCC=C)CC1=CNC2=CC=CC=C12)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenched with saturated brine (5 ml). The methylene chloride layer was separated, dried with magnesium sulfate and filtered then the volatiles removed under reduced pressure to leave a dark brown oil. Chromatography of this oil on silica gel using ethyl acetate and hexanes 2:1 v/v afforded 322 mg (84.5%) of the desired product. FAB-MS:- calculated for C26H29N3O5 463.2; found 464.5 (M+1). |
Here is a chemical reaction formula: Reactants are m2_m3:CS(=O)(=O)Cl, amount is: 0.0 ;m2_m3:C(C)N(CC)CC, amount is: 0.0 ;m4:C(C)N, amount is: 0.0 ;m1_m5:OCC1=CC=C(C=C1)C1=C(C=CC=C1)CNC(=O)OC(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m10:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m5:C(Cl)Cl, amount is: 0.0 MOLE;m8:C(C)(=O)OCC, amount is: 0.0 MOLE;m9:C(C)(=O)OCC, amount is: 0.0 MOLE;m7:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)NCC1=CC=C(C=C1)C1=C(C=CC=C1)CNC(=O)OC(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Hydroxymethyl-2'(t-butoxycarbonylaminomethyl)-1,1'-biphenyl (70 mg; 0.224 mmol) was dissolved in dry methylene chloride and stirred at 0° C. in an iced water bath and methanesulfonyl chloride (22 μl; 0.285 mmol) and triethylamine (39 μl; 0.280 mmol) added. The reaction mixture was stirred for 3 h at 0° C. and then 70% aqueous ethylamine (5 ml) added. The mixture was stirred for 5 h at room temperature vigorously, then partitioned between water and methylene chloride. The organic phase was separated and the aqueous layer extracted with methylene chloride (2×25 ml). The combined methylene chloride layers were dried over potassium carbonate powder, filtered and evaporated under reduced pressure to leave a thick viscous oil. The oil was subjected to a short column chromatography using a solvent gradient initially of ethyl acetate and hexanes (1:1 v/v) then neat ethyl acetate and finally with ethyl acetate and methanol (3:1 v/v). This afforded 52 mg (68%) of the desired product. FAB-MS:- calculated for C21H28N2O2 340.2 found 341.1 (M+1). |
Here is a chemical reaction formula: Reactants are m1_m3:C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@@H](C(=O)N(C1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])C)CCC1=CC=CC=C1, amount is: 0.0 ;m2:NCC1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N[C@@H](C(=O)N(C1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-])C)CCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The FMOC amide from Step F (1.15 g; 1.88 mmol) was dissolved in methylene chloride (10 ml) and 4-(aminomethyl)piperidine (1 ml) added. The reaction mixture was stirred at room temperature. The reaction mixture was stirred for 15 minutes and then quenched by adding water. The methylene chloride phase was separated, dried over ahnydrous potassium carbonate powder, filtered and evaprated under reduced pressure to afford an orange-yellow oil. The oil was chromatographed on silica gel using an eluant of ethyl acetate and methanol (9:1 v/v). A pale yellow oil (517 mg; 70.6%) was isolated of the amine. FAB-MS:- calculated for C23H23N3 O3 389.2 found 389.9 (M). |
Here is a chemical reaction formula: Reactants are m0_m1_m3_m4_m5:P(=O)([O-])([O-])[O-].[NH4+].[NH4+].[NH4+], amount is: 0.0 MOLE;m0_m1_m3_m4_m5:[Cl-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m0_m1_m3_m4_m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:P(=O)([O-])([O-])O.[NH4+].[Na+];0:[Cl-].[NH4+];0:P(=O)([O-])([O-])O.[NH4+].[NH4+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium ammonium phosphate and ammonium chloride are prepared from an ammonium phosphate (e.g., diammonium phosphate) and sodium chloride in water. The crystallization of sodium ammonium phosphate may take place between -10° C. to 40° C. Using the present invention, technical grade sodium ammonium phosphate and ammonium chloride can be produced from fertilizer grade diammonium phosphate. |
Here is a chemical reaction formula: Reactants are m3:S(=O)(=O)([O-])[O-].[Na+].[Na+], amount is: 0.0 MOLE;m2:[Cl-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:S(=O)(=O)([O-])[O-].[NH4+].[NH4+];0:[Na+].[Cl-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: It is also known that ammonium chloride and sodium sulphate can be produced from ammonium sulphate and salt (NaCl). According to this reaction, one would expect to produce disodium phosphate and ammonium chloride from sodium chloride and diammonium phosphate if the Na/P molar ratio is 2. |
Here is a chemical reaction formula: Reactants are m2_m5:C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-].[Na+], amount is: 0.0 MOLE;m4:C1=CC=C(C=C1)C2=COC3(C2=O)C4=CC=CC=C4C(=O)O3, amount is: 0.0 MOLE;m3:Cl.Cl.C(CN)N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m5:C(C)(=O)[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(CN)N;0:C1CC(CCC1CN2C(=O)C=CC2=O)C(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-].[Na+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sulfo-SMCC (1 eq.)(Pierce Chemical Co., Rockford, Ill.) is dissolved in sodium acetate buffer (pH 7) and ethylenediamine dihydrochloride (5 eq.) is added. The reaction is monitored by TLC visualized with fluorescamine. When reaction is complete the reaction mixture is applied directly to a C18 reverse-phase HPLC column and eluted with a gradient of acetonitrile in triethanolamine/water, pH 7. The excess ethylene diamine elutes at the solvent front, followed by the desired product. A small amount of double coupled material formed by the condensation of one molecule of ethylenediamine with two molecules of sulfo-SMCC elutes last. The desired material is characterized by 1H NMR and IR spectroscopy, mass spectrometry, and elemental analysis. |
Here is a chemical reaction formula: Reactants are m2:N[C@@H](CS)C(=O)O, amount is: 0.0 MOLE;m3:C(C)(=O)SCC[N+](C)(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:SCC[N+](C)(C)C;0:C(C)(=O)N[C@@H](CS)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: reacting the cysteine with the acetylthiocholine to form thiocholine and N-acetylcysteine, each in a concentration of about 0.2 molar to about 3.0 molar and in a molar ratio of thiocholine to N-acetylcysteine of 1:1.2 to 1.2:1. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:BrCCBr, amount is: 0.0 ;m1_m2_m3:S(=O)([O-])[O-].[Na+].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CS(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1,2-dibromoethane (37.6 g, 0.20 mol) and sodium sulfite (63.0 g, 0.5 mol) in water (225 mL) was heated at reflux temperature for 20 h. After the mixture was cooled in the refrigerator, crystals were collected. The crude product was repeatedly recrystallized from water-ethanol. The trace amount of inorganic salts was removed by treating the aqueous solution with a small amount of silver(I) oxide and barium hydroxide. The basic solution was neutralized with Amberlite-120 ion-exchange resin and treated three times with Amberlite-120 (sodium form) ion-exchange resin. After removal of the water, the product was recrystallized from water-ethanol to afford the title compound (30.5 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:BrCCCBr, amount is: 0.0 ;m1_m2_m4:S(=O)([O-])[O-].[Na+].[Na+], amount is: 0.0 ;m3:C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(CCS(=O)(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: This compound was prepared by a modification of the method described in Stone, G. C. H. (1936) J. Am. Chem. Soc., 58:488. 1,3-Dibromopropane (40.4 g, 0.20 mol) was treated with sodium sulfite (60.3 g, 0.50 mol) in water at reflux temperature for 48 h. Inorganic salts (sodium bromide and sodium sulfite) were removed by successive treatment of the resultant reaction mixture with barium hydroxide and silver(I) oxide. The solution was then neutralized with Amberlite-120 (acid form) and decolorized with Norit-A. Barium ions were removed by treatment of the aqueous solution with Amberlite-120 (sodium form) ion-exchange resin. The solvent was removed on a rotary evaporator, and the crude product was recrystallized from water-ethanol several times to give the title compound (42.5 g). The small amount of trapped ethanol was removed by dissolving the crystals in a minimum amount of water and then concentrating the solution to dryness. The pure product was further dried under high vacuum at 56° C. for 24 h: mp>300° C.; 1H NMR (D2O) δ: 3.06-3.13 (m, 4H, H-1 and H-3), 2.13-2.29 (m, 2H, H-2); 13C NMR (D2O) δ: 52.3 (C-1 and C-3), 23.8 (C-2). |
Here is a chemical reaction formula: Reactants are m1_m4_m2:C(C#CCC)O, amount is: 0.0 ;m1_m4_m2:C1(=CC=C(C=C1)S(=O)(=O)Cl)C, amount is: 0.0 ;m3:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:[Cl-].[Na+].O, amount is: 0.0 ;m1_m4_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=C(C=C1)S(=O)(=O)OCC#CCC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-pentyn-1-ol (8.40 g, 100 mmol) in THF (60 mL) was treated with p-toluenesulfonyl chloride (23.9 g, 125 mmol) at -10° C., followed by pulverized KOH (11.3 g, 200 mmol) without allowing the temperature to exceed -5° C. After 1.5 hours of stirring at -10° C., 50 mL of saturated brine was added and the product extracted into CH2Cl2. The product, 2-pentyn-1-yl p-toluenesulphonate (2), was isolated by flash chromatography (18.17 g 76.4% yield). 1H NMR (200 MHz) δ: 7.81 (d, J=8.4 Hz, 2H, arom. CH), 7.33 (d, J=7.9 Hz, 2H, arom. CH), 4.68 (t, J=2.2, 2.2 Hz, 2H, CH2O-1), 2.44 (s, 3H, arom. CH3), 2.13 (tq, J=2.2, 2.2, 2.2, 7.5, 7.5 Hz, 2H, CH2 -4), 1.00 (t, J=7.5, 7.5 Hz, 3H, CH3 -5). |
Here is a chemical reaction formula: Reactants are m3:CCCCCC, amount is: 0.0 ;m1:O1C(CCCC1)OCCCC#C, amount is: 0.0 ;m2:C(CCC)[Li], amount is: 0.0 MOLE;m4_m5:C(CCCC)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5:CN1CCCN(C1=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O1C(CCCC1)OCCCC#CCCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-(Tetrahydopyran-2-yloxy)-4-pentyne (1) (0.66 g, 3.90 mmol) was metallated with n-butyllithium solution (2.5M) in hexane (1.87 ml, 1.2 eq.). Addition of a solution of n-pentyl bromide (0.725 ml, 1.5 eq.) in DMPU (2 ml) produced 0.54 g (58% yield) of the title compound (15). 1H NMR (200 MHz) δ: 4.60 (m, 1H, CH-2'), 3.65 (m, 4H, CH2 -1, 6'), 2.26 (tt, J=7.0, 7.0, 2.0, 2.0 Hz, 2H, CH2 -3), 2.13 (tt, J=7.0, 7.0, 2.5, 2.5 Hz, 2H, CH2 -6), 1.77 (tt, J=6.8, 6.8, 7.07 7.0 Hz, 2H, CH2 -2), 1.33 (m, 6H, CH2 -7, 8, 9), 1.52 (m, 6H, CH2 -3', 4', 5'), 0.89 (t, J=7.0 Hz, 3H, CH3). MS [FAB, m/z(%)] 237 (M+ -1), 85 (100). IR (CCl4, cm-1) 2229, 1322, 1331, 1201, 1138, 1121, 1034. |
Here is a chemical reaction formula: Reactants are m1:O1C(CCCC1)OCCCC#CCCCCC, amount is: 0.0 ;m2:[Ni], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)[O-].[Ni+2].C(C)(=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-(Tetrahydropyran-2-yloxy)-4-decyne (15) (0.5 g, 2.1 mmol), prepared according to Example 13, was hydrogenated in ethanol (20 ml) over P2-Ni, formed from nickel acetate (75 mg) deactivated with ethylenediamine (0.2 ml) for 4 hr. After chromatography on silica gel, the product (16) (0.43 g) was obtained in 85% yield. GC (Rt): starting material 15, 22.18 min, 0.4%; desired product 16 21.59 min, 97.9%; the 4E isomer of 16, 21.75 min, 1.7%. 1H NMR (200 MHz ) δ: 5.37 (m, 2H, CH=CH-4, 5), 4.58 (m, 1H, CH-2'), 3.60 (m, 4H, CH2 -1, 6'); 2.12 (M, 2H, CH2 -6); 2.04 (m, 2H, CH2 -3); 1.16 (tt, 2H, J=6.8, 6.8, 7.0, 7.0 Hz, CH2 -2), 1.4-1.9 (m, 6H, CH2 -3', 4', 5'), 1.29 (m, 6H, CH2 -7, 8, 9); 0.88 (t, 3H, J=7.0 Hz, CH3). IR (CCl4, cm-1) 3007, 1653, 1201, 1138, 1120 1034. MS [FAB, m/z(%)] 239 (M+ -1), 85 (100). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:[Cl-].[Ca+2].[Cl-], amount is: 0.0 MOLE;m1_m2_m3:[O-]P([O-])(=O)OP(=O)([O-])[O-].[Na+].[Na+].[Na+].[Na+], amount is: 0.0 MOLE;m1_m2_m3:[Ca].[P], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:O.O.[O-]P([O-])(=O)OP(=O)([O-])[O-].[Ca+2].[Ca+2], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: An aqueous calcium chloride solution and an aqueous sodium pyrophosphate solution were mixed together so that the calcium/phosphorus atomic ratio became 1:1, and the mixture was allowed to stand for a whole day to form calcium diphosphate dihydrate (Ca2P2O7.2H2O) crystals, which were then filtered off. The thus prepared material was packed into a column in the same manner as in Example 1, and a mixed sample of serum albumin, lysozyme and cytochrome c was chromatographed thereon. As a result the serum albumin flowed through the column without being retained therein, while the lysozyme and cytochrome c were retained therein. |
Here is a chemical reaction formula: Reactants are m4:NC1=CC=C2CCC=3C=CC=C1C32, amount is: 0.0 MOLE;m5:C1(=CC=CC=C1)NC1=CC=C2CCC=3C=CC=C1C32, amount is: 0.0 MOLE;m1_m6_m2_m3:IC1=CC=CC=C1, amount is: 0.0 ;m1_m6_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m6_m2_m3:[N+](=O)([O-])C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m1_m6_m2_m3:[Cu], amount is: 0.0 .Products are 0:C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C2CCC=3C=CC=C1C32, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 33.85 g (0.2 mol) of 5-aminoacenaphtthene was mixed with 102.1 g (0.5 mol) of iodo benzene, 1.3 g (0.02 mol) of copper powder, 34.5 g (0.25 mol) of anhydrous potassium carbonate and 100 ml of nitrobenzene, and the mixture was stirred at 200° C. for 26 hours. The reaction was determined to be finished when disappearance of 5-aminoacenaphthene and 5-(N-phenylamino)acenaphthene as an intermediate was identified. 300 ml of toluene was added thereto to dissolve a product, and the resultant mixture was filtrated and concentrated. The concentrated product was purified by column chromatography (carrier: silica gel, eluent: toluene/hexane=1/4) to obtain 48.7 g (yield: 75.7%, melting point: 168.5°-170.5° C.) of 5-(N,N-diphenylamino)acenaphthene. |
Here is a chemical reaction formula: Reactants are m2:[O-]P([O-])(=O)OP(=O)([O-])[O-], amount is: 0.0 ;m1:C(CCCCC#N)#N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(#N)CCCCC(=O)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Various Pseudomonas strains were grown on 10 mM adipontrile in PR Basal medium for 24 h and harvested by centrifugation. Wet cell pastes were frozen for storage. To test for biocatalyst reaction, 50 mg of frozen cell paste was resuspended in 1 mL of 50 mM pyrophosphate buffer, pH 7.5. Adiponitrile substrate was added to a final concentration of 100 mM and the cell suspensions were shaken at 200 rpm at 5° C. for 4-7 h. Cells were removed by centrifugation and the clarified supernatant was analyzed for the presence of 5-cyanopentanamide by gas chromatography. The following Pseudomonas strains were found to produce the desired product: P. putida 5B-MGN-2p (NRRL-18668), Pseudomonas sp. 3L-H-2-6-1p, P. putida 20-5-SBN-1b (ATCC 55735), P. putida 3L-G-1-5-1a-1 (ATCC 55736), P. chlororaphis B23 (FERM-B187), Pseudomonas sp. 3L-H-9-6-2p, and P. putida 2-H-9-5-1a. |
Here is a chemical reaction formula: Reactants are m2_m3_m4_m5:N[C@@H](C)C(=O)O, amount is: 0.0 MOLE;m2_m3_m4_m5:N[C@@H](CC1=CC=CC=C1)C(=O)O, amount is: 0.0 MOLE;m2_m3_m4_m5:N[C@H](C)C(=O)O, amount is: 0.0 MOLE;m2_m3_m4_m5:C1(=CC=CC=C1)CC(C(=O)[O-])=O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N[C@H](CC1=CC=CC=C1)C(=O)O;0:N[C@@H](CC1=CC=CC=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Using cultures of recombinant cells of the present invention with the addition of D-, L-alanine and L-phenylalanine as additional sources of D-alanine and phenylpyruvate substrates for the D-aminotransferase gene product resulted in the production of 13.66 g/l of D-phenylalanine and 0.47 g/l of L-phenylalanine, a 94% enantiomeric excess. In the case where only D-, L-alanine was added to the cultures during the fermentation process resulted in the production of 4.15 g/l of D-phenylalanine and no L-phenylalanine, a 100% enantiomeric excess. In contrast, when no D-, L-alanine or L-phenylalanine was added to the cell cultures during the fermentation process, 1.12 g/l of D-phenylalanine and 0.47 g/l of L-phenylalanine is produced, a 41% enantiomeric excess. |
Here is a chemical reaction formula: Reactants are m2:O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO, amount is: 0.0 MOLE;m3:N[C@@H](C)C(=O)O, amount is: 0.0 MOLE;m4:N[C@@H](C)C(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:N[C@H](CC1=CC=CC=C1)C(=O)O;0:N[C@@H](CC1=CC=CC=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The amount of glucose fed was 2021 g over 52 hours. The fermentation medium included a D-, L-alanine feed whereby a total of 1400 mls of 167 g/l D-, L-alanine was fed at a rate of 1.9 ml/min starting 12 hrs from the beginning of the fermentation. In addition, L-phenylalanine was fed at the same concentration and rate as the D-, L-alanine. The fermentation resulted in 13.66 g/l of D-phenylalanine and 0.87 g/l L-phenylalanine being produced. |
Here is a chemical reaction formula: Reactants are m2:C=1N=C(C2=C(N1)N(C=N2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)N, amount is: 0.0 MOLE;m3:C1=NC2=C(N1[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)NC(=NC2=O)N, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O;0:C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)NC(=NC2=O)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The enzyme of the present invention isolated and purified from rat cerebral cortex in Example was acted on [8-3H] cAMP and [8-3H] cGMP as substrates to form [8-3H] 5'-AMP and [8-3H] 5'-GMP, respectively. The products were reacted with 5'-nucleotidase to form [8-3H] adenosine and [8-3H] guanosine, respectively. These products were separated from each other on a cation exchange resin column (AG50 W-X4, Bio-Rad) to assay for the radioactivity. The assay was carried out in a manner similar to that of the enzymatic activity described in Example. |
Here is a chemical reaction formula: Reactants are m2:C1CO1, amount is: 0.0 ;m1:CNCCCCCCCCCCCCCCCCCC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:OCCN(C)CCCCCCCCCCCCCCCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: An autoclave provided with a stirrer, a thermometer, a pressure gauge and a pressure dropping funnel was charged with 250 g of N-methyloctadecylamine and heated to 160° C. Then 45 g of ethylene oxide was occasionally added dropwise thereto under a pressure of 0 to 6 kg/cm2G. Three hours were required for completing the addition. Next, the resulting mixture was aged, i.e., maintained, at 160° C. for 2 hours and then cooled. The reaction mixture was taken out and distilled to thereby give 250 g of N-(2-hydroxyethyl)-N-methyloctadecylamine. This product had a boiling point of 185° to 190° C./0.2 mmHg. |
Here is a chemical reaction formula: Reactants are m1_m2:OCCN(C)CCCCCCCCCCCCCCCCCC, amount is: 0.0 ;m1_m2:C(CCCCCCCCCCCCCCCCC)(=O)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(CCCCCCCCCCCCCCCCC)(=O)OCCN(C)CCCCCCCCCCCCCCCCCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A four-neck flask provided with a stirrer, a thermometer and a dehydrating tube was charged with 200 g of the N-(2-hydroxyethyl)-N-methyloctadecylamine and 174 g of octadecanoic acid. The mixture was heated to 180° C. and maintained at this temperature for 12 hours while distilling off the water thus formed. Thus 350 g of N-(2-octadecanoyloxyethyl)-N-methyloctadecylamine was obtained. Based on the NMR and IR spectra, it was confirmed that this product had the following structure. This compound will be referred to as the enhancer 25 hereinafter. ##STR31## |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC=C, amount is: 0.0 ;m1_m4_m2_m3:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 ;m1_m4_m2_m3:ClC=1C=C(C(=O)OO)C=CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC1CO1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 500 mg (1.48 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3-butenyl)-3H- 1,2,4-triazol-3-one in 20 mL of dichloromethane was added 172 mg (1.63 mmol) of sodium carbonate and 970 mg of m-chloroperoxybenzoic acid (50-60%, 2.81 mmol) in an ice bath. The reaction mixture was stirred at room temperature for 24h. The mixture was filtered and the filtrate was evaporated in vacuo to give 500 mg of the title compound of Step 3 as yellow solid. The crude product was used in the following reaction without further purification. 1H NMR (CDCl3, 400 MHz) δ 11.25 (s,1H), 7.55 (s,1H), 7.2 (s,1H), 4.8 (s,2H), 3.05 (m,1H), 2.8 (t,1H), 2.8 (t,2H), 2.6 (s,1H), 2.75 (d,1H), 2.2 (m,1H), 1.8 (m,1H). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C(NC1=O)CCC1CO1, amount is: 0.0 ;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)O)C1=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 500 mg (1.41 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one and 563 mg (4.08 mmol) of potassium carbonate in 20 mL of acetonitrile was warmed at reflux for 2h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 184 mg of the title product of Step 4 as a pale yellow foam, 1H NMR (CDCl3, 400 MHz) δ 7.5 (s,1H), 7.15 (s,1H), 4.8 (s,2H), 4.45 (broad t,1H), 3.8 (m,2H), 3.0 (m,1H), 2.8 (m,1H), 2.6 (s,1H), 2.2 (s,1H), 2.15 (m,1H), 1.95 (m,1H). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)O)C1=O, amount is: 0.0 ;m1_m3_m2:C(C)N(CC)S(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CC(CC2)F)C1=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 169 mg (0.477 mmol) of 5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-6-hydroxy-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one in 5 mL of dichloromethane was added 76 μl (0.573 mmol) of diethylaminosulfur trifluoride (DAST) at 0° C. The reaction mixture was stirred at 0° C. for 1h. The mixture was then quenched with ice and extracted with dichloromethane. The organic extracts were dried (MgSO4), and then concentrated in vacuo to give a pale red solid. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 64 mg of the title product as a pale yellow foam. 19F NMR (CDCl3, 400 MHz) δ-188 ppm, 1H NMR (CDCl3, 400 MHz) δ 7.5 (s,1H), 7.1 (s,1H), 5.2 (m,1H), 4.8 (s,2H), 4.2-3.6 (m,2H), 3.2-3.0 (m,1H), 3.0-2.6 (m,1H), 2.5 (s,1H), 2.3-1.8 (m,2H). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C)(=O)OC=1C(=CC(=C(C1)N1N=C2N(CCCC2)C1=O)Cl)Cl, amount is: 0.0 ;m1_m3_m2:BrN1C(CCC1=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)OC=1C(=CC(=C(C1)N1N=C2N(CCCC2Br)C1=O)Cl)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3.55 g (10.4 mmol) of 5,6,7,8-tetrahydro-2-(5-acetyloxy-2,4-dichlorophenyl)-1,2,4-triazolo[4,3-α]pyridin-3(2H)-one in 100 mL of carbon tetrachloride was added 2.03 g (11.4 mmol) of N-bromosuccinimide at room temperature. The mixture was warmed under reflux by irradiating with a sun lamp for 3h. The mixture was cooled to room temperature and concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel, eluting with a 1:1 v:v mixture of ethyl acetate and n-hexane to give 4.10 g of the title product of Step 1 as a white solid, m.p.: 75°-83° C.; 1H NMR (CDCl3, 300 MHz) δ 7.6 (s,1H), 7.35 (s,1H), 5.25 (m,1H), 4.0 (m,1H), 3.6 (m,1H), 2.75 (s,3H), 2.5-1.9 (m,4H). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CCCC2O)C1=O, amount is: 0.0 ;m1_m3_m2:C(C)N(CC)S(F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C(C(=C1)Cl)OCC#C)N1N=C2N(CCCC2F)C1=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 300 mg (0.847 mmol) of 5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-8-hydroxy-1,2,4-triazolo[4,3-α]pyridin-3(2H)-one in 10 mL of dichloromethane was added 123 mL (0.930 mmol) of diethylaminosulfur trifluoride (DAST) at -78° C. The reaction mixture was stirred at -78° C. for 4h. The mixture was warmed to room temperature, quenched with ice, and extracted with dichloromethane. The organic layers were dried (MgSO4), and concentrated under reduced pressure. The crude product was flash chromatographed over silica gel, eluting with a 98:2 v:v mixture of dichloromethane and methanol to give 272 mg of the title product of Step 4 as a yellow solid. 19F NMR (CDCl3, 300 MHz) δ-172; 1H NMR (CDCl3, 300 MHz) δ 7.55 (s,1H), 7.2 (s,1H), 5.6, 5.5 (2m, J=70 Hz,1H), 4.8 (s,2H), 4.0 (m,1H), 3.55 (m,1H), 2.6 (m,1H), 2.5-1.8 (m,4H). |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:[OH-].[Na+], amount is: 0.0 ;m1_m3_m2_m4:C(C)OP(=O)(C(CC(=O)OCC)P(=O)(OCC)OCC)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:O, amount is: 0.0 ;m1_m3_m2_m4:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O(CC)P(=O)(C(CC(=O)O)P(=O)(OCC)OCC)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of NaOH (4.00 g, 100 mmol) in water (50 ml) was added to a solution of ethyl 3,3-bis(diethoxyphosphinyl)propionate (32.6 g, 87 mmol) in EtOH (100 ml), and heated at 80° C. for 1 hour. After cooling, the EtOH was evaporated, and the residue was acidified to methyl orange with 12N HCl. The product was extracted into dichloromethane (5×50 ml). The organic layer was dried (Na2SO4) and concentrated to give the title compound (28.8 g, 96%) as a viscous oil. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 ;m1_m4:C(CC)N(C(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O)CCC, amount is: 0.0 ;m2:B.CSC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)OP(OCC)(=O)C(CCN(CCC)CCC)P(OCC)(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N,N-dipropyl-3,3-bis(diethoxyphosphinyl)propionamide (1.25 g, 2.9 mmol) in THF (7.1 ml) was cooled to 0° C., and borane-methylsulfide (0.71 ml, 7.1 mmol) was added via syringe. The reaction was stirred at 0° C. for 20 minutes, then warmed at 65 C. for 3 hours. The reaction mixture was cooled to 0° C. and 6N HCl (6 ml) was added carefully. The solvent was removed m vacuo, and the residue was treated with methanol (5 ml) and concentrated. The residue was dissolved in water (10 ml) and extracted with Et2O (3×10 ml). The aqueous layer was made basic to phenolphthalein with solid KOH and saturated with NaCl. The product was extracted into dichloromethane (5×20 ml), dried (Na2SO4) and concentrated to give the title compound (0.71 g, 60%). |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m5:CON(C(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O)C, amount is: 0.0 ;m1_m4_m2_m5:[H-].[Na+], amount is: 0.0 ;m1_m4_m2_m5:C1CCOC1, amount is: 0.0 ;m1_m4_m2_m5:C1CCOC1, amount is: 0.0 ;m3:[H-], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:O=C(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N-methoxy-N-methyl-3,3-bis(diethoxyphosphinyl)propionamide (1.00 g, 2.6 mmol) in THF (5 ml) was slowly added to a slurry of 80% sodium hydride (80 mg, 2.7 mmol) in THF (10 ml) at 0° C. Stirring was continued until all of the hydride was consumed (~20 minutes). The solution was cooled to -78° C. and ethylmagnesium bromide (1.0 ml of a 3.0M solution in diethyl ether, 3.0 mmol) was added. After the addition, the reaction mixture was warmed to 0° C. and stirred for one hour. The reaction was quenched by pouring slowly into a well-stirred ice-cold mixture of ethanol (40 ml) and concentrated HCl (5 ml). The solvents were removed in vacuo, the residue was taken up in brine (20 ml) and extracted with dichloromethane (4×20 ml). The combined extracts were dried (Na2SO4), concentrated in vacuo, and the resulting oil was purified by flash chromatography on silica gel eluting with 10% i-propanol in ethyl acetate to give the title compound (0.50 g, 54%) as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are m4:[BH3-]C#N.[Na+], amount is: 0.0 ;m1_m6_m2_m3:O=C(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CC, amount is: 0.0 ;m1_m6_m2_m3:CC1=C(C(=C(C=C1C2(C3=CC=CC=C3S(=O)(=O)O2)C4=CC(=C(C(=C4C)Br)O)C(C)C)C(C)C)O)Br, amount is: 0.0 MOLE;m1_m6_m2_m3:C(C1=CC=CC=C1)N, amount is: 0.0 ;m5:[BH3-]C#N.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:C(C)(=O)O, amount is: 0.0 MOLE;m1_m6_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)NC(CC(P(OCC)(=O)OCC)P(OCC)(=O)OCC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of tetraethyl 3-oxopentane-1,1-bisphosphonate (0.50 g, 1.4 mmol) in methanol (5 ml) was added a small amount of bromothymol blue and benzylamine (0.75 g, 7.0 mmol). Acetic acid was added dropwise until the solution turned yellow (pH=6), and NaCNBH3 (57 mg, 0.9 mmol) was added. The resulting yellow solution was stirred at room temperature for 2 days, at which time more NaCNBH3 (20 mg) was added. After stirring a total of 4 days, the reaction was quenched by adding concentrated HCl until the pH was less than 1, and the solvents were removed in vacuo. The residue was taken up in water (10 ml) and washed with diethyl ether (2×20 ml). The aqueous layer was made basic (pH greater than 10) by the addition of solid KOH, saturated with NaCl, and extracted with dichloromethane (5×25 ml). The combined extracts were dried (Na2SO4) and concentrated to give tetraethyl 3-benzylaminopentane-1,1-bisphosphonate. This material was hydrolyzed by heating at reflux in concentrated HCl (6 ml) for 20 hours. The volatiles were removed under vacuum, the residue dissolved in water (10 ml) and concentrated under vacuum to give 0.49 g of Compound No. 159 as a hygroscopic foam. |
Here is a chemical reaction formula: Reactants are m1_m7_m2_m8:C(P(OCC)(OCC)=O)P(OCC)(OCC)=O, amount is: 0.0 ;m1_m7_m2_m8:[H-].[Na+], amount is: 0.0 ;m6:[Cl-].[Na+], amount is: 0.0 MOLE;m4_m9_m5:C(CCC)NC(CCl)=O, amount is: 0.0 ;m4_m9_m5:[I-].[K+], amount is: 0.0 ;m3:[H-], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m7_m2_m8:C1CCOC1, amount is: 0.0 ;m1_m7_m2_m8:C1CCOC1, amount is: 0.0 ;m4_m9_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)NC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tetraethyl methylenebisphosphonate (1.44 g, 5.0 mmol) in THF (1 mL) was added to a slurry of 80% sodium hydride (150 mg, 5.0 mmol) in THF (4 mL) at 0° C. The reaction was warmed to room temperature and stirred until all of the hydride was consumed. A solution of N-butyl-2-chloroacetamide (0.75 g, 5.0 mmol) in THF (1 ml) and potassium iodide (100 mg) were then added. The reaction mixture was then heated at 50° C. for 18 hours, during which time sodium chloride precipitated. Additional sodium hydride (20 mg) was added, and the reaction mixture was heated an additional 4 hours. After cooling, the mixture was poured into 1N HCl (10 mL) and diethyl ether (50 mL) was added. The diethyl ether layer was further extracted with water (3×10 mL). The combined aqueous fractions were extracted with dichloromethane (4×25 mL). The combined extracts were dried (Na2SO4) and concentrated to give the title compound (1.40 g, 70%) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m4:C(CCC)NC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=O, amount is: 0.0 ;m3:Cl, amount is: 0.0 ;m2:B.CSC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCC)NCCC(P(O)(=O)O)P(O)(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N-butyl-3,3-bis(diethoxyphosphinyl)propionamide (1.40 g, 3.5 mmol) in THF (9 mL) was cooled to 0° C., and borane-methyl sulfide (0.90 ml, 9.0 mmol) was added via syringe. The reaction was stirred at 0° C. for 5 minutes, then warmed to 65° C. for 3 hours. The reaction mixture was cooled to 0° C. and 6N HCl (6 ml) was added carefully. The solvent was removed in vacuo, and the residue was repeatedly concentrated from methanol (3×10 mL). The product was dissolved in 12N HCl and heated at reflux for 20 hours. After cooling, the volatile materials were removed under vacuum, the residue was dissolved in water (10 mL) and then concentrated to give 1.05 g of Compound No. 158 as a hygroscopic glass. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3_m5:C(C1=CC=CC=C1)(=O)Cl, amount is: 0.0 ;m1_m4_m2_m3_m5:NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC, amount is: 0.0 ;m1_m4_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3_m5:ClCCl, amount is: 0.0 MOLE;m1_m4_m2_m3_m5:ClCCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)(=O)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of benzoyl chloride (0.73 g, 5.0 mmol) in dichloromethane was added slowly to a solution of tetraethyl 5-aminopentane-1,1-bisphosphonate (1.50 g, 4.5 mmol) from Example 11, part A, and triethylamine (0.76 mL, 5.5 mmol) in dichloromethane at 0° C. After warming to room temperature for 30 minutes, the reaction was quenched by addition of 1N HCl (30 mL). The product was extracted into dichloromethane (2×20 mL) and the combined organic layers were washed with saturated NaHCO3 (2×15 mL), dried (Na2SO4), and concentrated in vacuo. Flash chromatography on silica gel eluting with 15% i-propanol in ethylacetate in EtOAc gave the title compound (0.64 g) as an oil. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 ;m1_m4:C(C1=CC=CC=C1)(=O)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC, amount is: 0.0 ;m2:CSC.B, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)NCCCCC(P(OCC)(=O)OCC)P(OCC)(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonate (0.63 g, 1.36 mmol) in THF (3.4 mL) was cooled to 0° C., and borane methylsulfide (0.34 ml, 3.4 mmol) was added via syringe. The reaction was stirred at 0° C. for 20 minutes, then warmed to 65° C. for 2.5 hours. The reaction mixture was cooled to 0° C. and 6N HCl (4.0 ml) was added carefully. The solvent was removed in vacuo, and the residue was concentrated repeatedly from methanol (2×5 mL). The residue was dissolved in water (10 ml) and extracted with diethyl ether (3×5 ml). The aqueous layer was made basic to phenolphthalein with solid KOH and saturated with NaCl. The product was extracted into dichloromethane (5×20 ml), dried (Na2SO4) and concentrated to give the title compound (0.28 g). |