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Here is a chemical reaction formula: Reactants are m1_m3_m2:CC(C)(C)NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C, amount is: 0.0 ;m1_m3_m2:C(=O)(C(F)(F)F)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NS(=O)(=O)C1=C(N(C=C1)C)C(=O)N(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5.63 g of 3-[[(1,1-dimethylethyl)amino]sulfonyl]-N,N,1-trimethyl-1H-pyrrole-2-carboxamide in 75 mL of methylene chloride was added 75 mL of TFA. The reaction mixture was allowed to stir at room temperature overnight ca. 16 hours. The reaction mixture was concentrated in vacuo. Three portions of diethyl ether were added to the residue and removed by evaporation to remove residual TFA, affording 4.21 g of the title compound as a gray solid, m.p. 185°-190.5° C. |
Here is a chemical reaction formula: Reactants are m3_m5:ClC(=O)OC, amount is: 0.0 ;m2:C(CCC)[Li], amount is: 0.0 ;m1_m4:CC(C)(C)NS(=O)(=O)C=1N(C=CC1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C1CCOC1, amount is: 0.0 ;m6:C(C)(=O)OCC, amount is: 0.0 ;m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)NS(=O)(=O)C=1N(C=CC1C(=O)OC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2.5 g (11.5 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-2-sulfonamide in 50 mL THF under nitrogen atmosphere cooled to below -70° C. was added dropwise 13 mL (32.5 mmol) of 2.5M n-butyllithium at such a rate as to keep the temperature below -58° C. After stirring at -20° C. to -10° C. for 30 min then 1 h at 0° C., the mixture was recooled to -70° C. and treated with a solution of 1.63 g (17.3 mmol) of methyl chloroformate in 6 mL THF causing an exotherm to -57° C. The reaction mixture was stirred overnight at ambient temperature then diluted with 200 mL of ethyl acetate. This solution was washed successively with two 60 mL portions of 1N HCl, brine, then dried (Na2SO4) and evaporated to a dark oil. The crude product was purified by chromatography on silica gel (30% ethyl acetate/70% hexanes) then collected from hexanes to afford 0.45 g of the title compound, m.p. 105°-108° C. |
Here is a chemical reaction formula: Reactants are m3:C1CCC2=NCCCN2CC1, amount is: 0.0 ;m2:COC1=NC(=NC(=N1)C)NC(OC1=CC=CC=C1)=O, amount is: 0.0 ;m1:NS(=O)(=O)C=1N(C=CC1C(=O)OC)C, amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1N=C(NN(C1)C)NC(=O)NS(=O)(=O)C=1N(C=CC1C(=O)OC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 2-(aminosulfonyl)-1-methyl-1H-pyrrole-3-carboxylate (0.10 g, 0.46 mmol) and 0.13 g (0.50 mmol) of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate were combined in 2 mL of acetonitrile and 0.075 mL of DBU was added and the resulting amber solution was stirred at ambient temperature for 30 min. The reaction mixture was diluted with 15 mL of water and acidified with 0.5 mL 1N HCl and the resulting precipitate was collected by filtration and rinsed successively with water and ether, then dried to afford 0.13 g oil the title compound as a white solid, m.p. 189°-190° C. (dec). |
Here is a chemical reaction formula: Reactants are m3:[OH-].[K+], amount is: 0.0 ;m1_m2_m4:NC1=C(C=O)C=CC=N1, amount is: 0.0 ;m1_m2_m4:CC(=O)C1=C(C=CC=C1F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(=CC=C1)F)C1=NC2=NC=CC=C2C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Aminonicotinaldehyde (2.44 g, 20 mmol) and 2,6-difluoroacetophenone (3.28 g, 21 mmol) are dissolved in 20 ml of MeOH. The mixture is treated dropwise with 3 ml of 40% KOH and, after the exothermic reaction has subsided, it is poured onto water and the residue which is deposited is filtered off with suction. 3.8 g (79% yield) of the desired product are obtained. M.p. 100°-103° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:NC1=C(C=O)C=CC=N1, amount is: 0.0 ;m1_m2_m4:C(C)(=O)C=1SC=CN1, amount is: 0.0 ;m3:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:S1C(=NC=C1)C1=NC2=NC=CC=C2C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Aminonicotinaldehyde (1.5 g, 12.3 mmol) and 2-acetylthiazole (1.64 g, 12.9 mmol) are dissolved in 12 ml of MeOH and the mixture is treated with 1.5 ml of 40% KOH. After 3 h, the reaction is complete and the mixture is poured onto water. The solid which is deposited is filtered off with suction, washed and dried. 1.22 g (yield 46%) of the desired product are obtained. M.p. 160°-165° C. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m3_m6:CC=1C=C(C=C(C1)C)S, amount is: 0.0 ;m1_m2_m5:[N+](=O)([O-])C1=C(C#N)C(=CC=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m2_m5:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m6:CN(C)C=O, amount is: 0.0 ;m1_m2_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2,6-dinitrobenzonitrile (1.4 g 7.2 mmol) and K2CO3 (1.1 g, 7.9 mmol) in 10 ml of DMF was chilled to 0° C. A solution of 3,5-dimethylthiophenol (1.1 g 0.0079 mmol) in 10 ml of DMF, was added dropwise over 30 min with stirring under nitrogen. After stirring an additional 30 min, the reaction mixture was poured into 150 ml of water and stirred for 1 hr. The solid was collected by vacuum filtration. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 1.64 g (80%) of 2-[(3,5-dimethylphenyl)thio]-6-nitrobenzonitrile: mp 155°-156° C. |
Here is a chemical reaction formula: Reactants are m2:OOS(=O)[O-].[K+], amount is: 0.0 MOLE;m1_m3:CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:O, amount is: 0.0 ;m1_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC=1C=C(C=C(C1)C)S(=O)C1=C(C#N)C(=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile (Example 18) (1.0 g, 3.9 mmol) was dissolved in 100 ml of methanol. A solution of OXONE®.dagger. (2.63 g, 4.3 mmol) in 15 ml of water was added dropwise with stirring. After stirring 1.5 h, the solid was removed by vacuum filtration and washed with 3×50 ml of methanol. The filtrate was concentrated to dryness and chromatographed on silica get (flash; Hex/EtOAc 2:1) to provide 0.5 g (47%) of 2-[(3,5-dimethylphenyl)sulfinyl]-6-fluorobenzonitrile: mp 146°-147° C. |
Here is a chemical reaction formula: Reactants are m1_m5:CC=1C=C(C=C(C1)C)SC1=C(C#N)C(=CC=C1)F, amount is: 0.0 ;m4:O, amount is: 0.0 ;m2:OOS(=O)[O-].[K+], amount is: 0.0 MOLE;m3:OOS(=O)[O-].[K+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC=1C=C(C=C(C1)C)S(=O)(=O)C1=C(C#N)C(=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile (Example 18) (1.0 g 3.9 mmol) was dissolved in 100 ml of methanol. A solution of OXONE®.dagger. (5.26 g, 8.6 mmol) in 30 ml of water was added dropwise with stirring. After stirring 1 h, another 1.5 equivalents of OXONE® (3.60 g 5.9 mmol) was added. The reaction was stirred for 18 h. The solid was removed by vacuum filtration and washed with 200 ml of methanol, then with 2×60 ml of acetone. The filtrate was concentrated to dryness and chromatographed on silica gel (flash; Hex/EtOAc 1:1) to provide 0.73 g (65%) of 2-[(3,5-dimethylphenyl)sulfonyl]-6-fluorobenzonitrile: mp 167°-168° C. |
Here is a chemical reaction formula: Reactants are m3_m0:CCOC(=O)C, amount is: 0.0 MOLE;m1_m4:CC=1C=C(C=C(C1)C)S(=O)C1=C(C#N)C(=CC=C1)F, amount is: 0.0 ;m2:N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=C(C#N)C(=CC=C1)S(=O)C1=CC(=CC(=C1)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-[(3,5-Dimethylphenyl)sulfinyl]-6-fluorobenzonitrile (Example 19) (0.4 g, 1.5 mmol) was dissolved in 40 ml of methanol and chilled to -78° C. Condensed ammonia (20 ml, 15.4 g, 905 mmol) was added and the mixture was heated to 150° C. in a sealed Parr bomb for 24 h. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 0.24 g (61%) of 2-amino-6-[(3,5-dimethylphenyl)sulfinyl]benzonitrile: mp 190°-191° C.; NMR (Me2SO-d6, 200 MHz) δ 2.32 (s, 6H), 6.48 (br s, 2H), 6.90 (apparent d, 1H), 7.11 (apparent d, 1H), 7.20 (m, 1H), 7.32 (m, 2H), 7.52 (apparent t, 1H); mass spec (CI) M+ +1=271. Anal. Calc. for C15H14N2OS: C, 66.64; H, 5.22; N, 10.36; S, 11.86. Found: C, 66.71; H, 5.27; N, 10.32; S, 11.84. |
Here is a chemical reaction formula: Reactants are m2:N, amount is: 0.0 ;m3_m0:CCOC(=O)C, amount is: 0.0 MOLE;m1_m4:CC=1C=C(C=C(C1)C)S(=O)(=O)C1=C(C#N)C(=CC=C1)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=C(C#N)C(=CC=C1)S(=O)(=O)C1=CC(=CC(=C1)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-[(3,5-Dimethylphenyl)sulfonyl]-6-fluorobenzonitrile (Example 20) (0.5 g 1.7 mmol) was dissolved in 80 ml of methanol and chilled to -78° C. Condensed ammonia (20 ml, 15.4 g, 905 mmol) was added and the mixture was heated to150° C. in a sealed Parr bomb for 24 h. Chromatography on silica gel (flash; Hex/EtOAc 1:1) provided 0.28 g (56%) of 2-amino-6-[(3,5-dimethylphenyl)sulfonyl]benzonitrile: mp 208°-209° C.;; NMR (Me2SO-d6, 200 MHz) δ 2.36 (s, 6H), 6.59 (br s, 2H), 7.10 (apparent d, 1H), 7.3-7.4 (m, 2H) 7.54 (apparent d, 1H), 7.58 (m, 2H); mass spec (CI) M+ +1=287. Anal. Calc. for C15H14N2O2S: C, 62.92; H, 4.93; N: 9.78; S, 11.20. Found: C, 63.02; H, 4.98; N, 9.72; S, 11.12. |
Here is a chemical reaction formula: Reactants are m2:S(=O)(Cl)Cl, amount is: 0.0 ;m1_m4:NC(C(=O)O)CC, amount is: 0.0 ;m3:C(C)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.NC(C(=O)OCC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A slurry of 2-aminobutyric acid (100 g, Aldrich) in absolute ethanol (300 ml) was stirred under nitrogen at 0° C. and thionyl chloride (120.8 g) was added dropwise. The reaction was stirred overnight at 0° C. and then gradually warmed to room temperature. The resulting white slurry was heated under reflux for 3 hours, left to cool for 10 minutes, then poured into chilled diethyl ether (600 ml), with hand stirring. The suspension was filtered and the solid product dried to give the desired product (150 g) as a white solid. 1H NMR consistent with proposed structure. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:Cl.NC(C(=O)OCC)CC, amount is: 0.0 ;m1_m2_m3_m5:S(=O)(=O)([O-])[O-].[Mg+2], amount is: 0.0 ;m1_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ;m4:C(C1=CC=CC=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)=NC(C(=O)OCC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of the product from step (a) (149.6 g), magnesium sulphate (74.3 g), and triethylamine (246 ml) in dichloromethane (1500 ml) was stirred at room temperature under nitrogen and benzaldehyde (94.9 g, Aldrich) was added dropwise. The mixture was stirred at room temperature for 3 hours then filtered. The filtrate was concentrated, triturated in diethyl ether, filtered and concentrated to yield the desired product as a yellow oil (174 g). 1H NMR consistent with the proposed structure. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClS(=O)(=O)O, amount is: 0.0 ;m1_m2_m3:NC(CO)(CC=CC)CC, 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:C(C=CC)C1(NC1)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Chlorosulphonic acid (18 mL) was added to a solution of the product from step (e) (32.3 g) in acetonitrile (100 ml) at least 9° C. When addition was complete, the mixture was warmed to room temperature. The resulting crystals were filtered off, washed with acetonitrile/pet. ether, dried, taken up in a mixture of 50% w/v aqu. KOH (100 mL) and water (55 mL) and distilled over KOH to give the desired product as a colourless oil (16.1 g). 1H NMR consistent with the proposed structure. |
Here is a chemical reaction formula: Reactants are m3:CCO, amount is: 0.0 MOLE;m4_m1_m2:NC(CO)(CO)CC, amount is: 0.0 ;m4_m1_m2:C(OCC)(OCC)=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m4_m1_m2:C[O-].[Na+], amount is: 0.0 .Products are 0:C(C)N1C(OCC1CO)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium methoxide (2.2 g, Aldrich) was added to a solution of 2-amino-2-ethyl-1,3-propanediol (100.0 g, Aldrich) and diethyl carbonate (169.0 g, Aldrich) This solution was refluxed in a Dean Stark apparatus until no more EtOH was collected. The reaction mixture was cooled, added acetone (200 ml) and allowed to stand overnite at room temperature. The resulting suspension was filtered to give 81.0 g of the desired product as a beige solid. 1H NMR consistent with the proposed structure. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:FC(CCI)(F)F, 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:[I-].FC(CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of triphenylphosphine (Aldrich, 11.7 g) and 3,3,3-trifluoropropyl iodid (Lancaster, 10 g) was vigorously refluxed in xylenes (75 mL) for 2 days. The solid which formed was filtered and washed with xylenes then air dried to yield a white solid (16.6 g). 1H NMR and elemental analysis are consistent with the proposed structure. |
Here is a chemical reaction formula: Reactants are m5:Cl, amount is: 0.0 MOLE;m2:C(C)N(CC)CC, amount is: 0.0 ;m1_m6:C(N)(=N)C1=CC=C(CN=[N+]=[N-])C=C1, amount is: 0.0 MOLE;m3:ClC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m4:ClC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6:C(Cl)Cl, amount is: 0.0 ;m7:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC(=N)C1=CC=C(CN=[N+]=[N-])C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The crystals from (ii) above were dissolved in 500 ml methylene chloride and the resulting solution was dried (K2CO3), filtered and 27 ml (194 mmol) triethyl amine was added. 25 ml Benzyl chloroformate was slowly added to the stirred solution while the reaction mixture was cooled in an ice bath. After 30 minutes an additional 2 ml benzyl chloroformate was added and stirring was continued for another 30 minutes. Subsequently, water was added and the aqueous phase was adjusted to pH 7 with 2M HCl. The organic phase was dried (MgSO4) and the solvent was removed in vacuo. 4-(benzyloxycarbonylamidino) benzyl azide was finally isolated as colorless crystals from ether/methylene chloride/hexane. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(C)(C)OC(=O)NCC1CCNCC1, amount is: 0.0 ;m1_m2_m3:C(C1=CC=CC=C1)OC(=O)NC(SC)=N, 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(C)(C)(C)OC(=O)NCC1CCN(CC1)C(NC(=O)OCC1=CC=CC=C1)=N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 7.8 g (36.4 mmole) of 4-(N-tert-butyloxycarbonylaminomethyl) piperidine and 8.98 g (40 mmole) of N-benzyloxycarbonyl-S-methylisothiourea was mixed in 25 mL ethanol. The mixture was heated at 60°-70° C. for six hours and left at room temperature for two days. The solvent was evaporated and the residue was dissolved in CH2Cl2. The organic layer was washed twice with 0.3M KHSO4 and once with brine. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using a stepwise gradient of CH2Cl2 /MeOH (100/0, 97/3, 95/5, 90/10) as eluent to yield 5.22 g (37%) of the title product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:OCCC1CCNCC1, amount is: 0.0 ;m1_m2_m3:C(C1=CC=CC=C1)OC(=O)NC(SC)=N, 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:C(C1=CC=CC=C1)OC(=O)NC(=N)N1CCC(CC1)CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 6.2 g (0.028 mol) of 4-hydroxyethyl piperidine and 3.6 g (0.028 mol) of N-benzyloxycarbonyl-S-methyl isothiourea in 50 ml of acetonitrile was refluxed overnight. Evaporation and flash chromatography on silica gel with ethyl acetate gave 3.5 g (41%) of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CO, amount is: 0.0 ;m1_m2_m4:C(C)N(CC)CC, amount is: 0.0 ;m3_m5:CS(=O)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)(=O)OCC.CCCCCCC, amount is: 0.0 ;m3_m5:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)COS(=O)(=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.7 g (2.53 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-hydroxymethyl pyrrolidine and 0.70 ml (5.05 mmole) triethylamine was dissolved in 15 ml diethyl ether/CH2Cl2 1/1 and the mixture was cooled to 0° C. 0.25 ml (3.29 mmole) methanesulphonyl chloride in 3 ml diethyl ether was slowly added and the reaction mixture was stirred at 0° C for three hours. The solvent was evaporated and the residue was dissolved in ethyl acetate and extracted with a 0.3M KHSO4 -solution. The water layer was washed once with CH2Cl2. The water layer was made neutral with 10M NaOH-solution and extracted twice with CH2Cl2. The combined organic layer was dried (Na2 SO4), filtered and evaporated to yield 0.450 g (50%) of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)COS(=O)(=O)C, amount is: 0.0 ;m1_m2_m4:[N-]=[N+]=[N-].[Na+], amount is: 0.0 ;m3:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CN=[N+]=[N-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.450 g (1.27 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine and 0.124 g (1.9 mmole) of sodium azide were dissolved in 10 ml dimethylformamide and heated to 60° C. for four hours followed by stirring at room temperature over night. Water was added and the mixture was extracted twice with toluene/ethyl acetate 2/1. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2 /MeOH 95/5 as eluent to yield 0.262 g (68%) of the product. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C1=CC=CC=C1)N1CC(CC1)CCl, amount is: 0.0 ;m1_m2_m4:[C-]#N.[Na+], amount is: 0.0 ;m3:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)CC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 16.8 g (0.08 mole) (3RS)-1-benzyl-3-chloromethyl pyrrolidine and 5.88 g (0.12 mole) of sodium cyanide was dissolved in 250 ml dimethyl sulfoxide. The mixture was stirred at 60° C. for two days and at room temperature for one week. Water was added and the mixture was extracted three times with ethyl acetate. The combined organic layer was washed with brine, dried (Na2SO4), filtered and evaporated to yield 14.7 g (92%) of the product. |
Here is a chemical reaction formula: Reactants are m3_m4_m5:O, amount is: 0.0 ;m3_m4_m5:[OH-].[Na+], amount is: 0.0 ;m3_m4_m5:O, amount is: 0.0 ;m1_m6:C(C1=CC=CC=C1)N1CC(CC1)CC#N, amount is: 0.0 ;m2_m7:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6:C(C)OCC, amount is: 0.0 ;m2_m7:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1CC(CC1)CCN, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 14.7 g (0.0734 mole) (3RS)-1-benzyl-3-cyanomethyl pyrrolidine dissolved in 220 ml diethyl ether was slowly added to a slurry of 2.94 g of lithium aluminium hydride in 74 ml diethyl ether under an argon atmosphere. The mixture was stirred over night,and 6 ml water, 18 ml 3.75M NaOH-solution and 6 ml water was added to the mixture. The slurry was dried from excess of water with Na2SO4 /cellite, filtered by suction and evaporated to yield 14.84 g (99%) of the product. |
Here is a chemical reaction formula: Reactants are m3:OS(=O)(=O)[O-].[K+], amount is: 0.0 MOLE;m1_m2_m4:C(C)(C)(C)OC(=O)NCCC1CNCC1, amount is: 0.0 ;m1_m2_m4:C(C1=CC=CC=C1)OC(=O)NC(SC)=N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC(=N)N1CC(CC1)CCN, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.18 g (0.0102 mole) (3RS)-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine and 2.81 g (0.0125 mole) N-benzyloxycarbonyl-S-methylisothiourea was dissolved in 30 ml toluene and heated to 60°-70° C. for eight hours followed by stirring at room temperature for one day. 0.3M KHSO4 -solution was added and the water layer was washed with a mixture of the toluene and ethyl acetate and left for 2 days under which time the Boc group was removed. The acidic water phase was made alkaline and extracted four times with CH2 Cl2. The combined organic layer was dried (Na2SO4), filtered and evaporated to yield 2.0 g (51%) of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)(C)(C)OC(=O)NCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:CO, amount is: 0.0 ,Catalysts are m3:[OH-].[OH-].[Pd+2], amount is: 0.0 .Products are 0:C(C)(C)(C)OC(=O)NCC1CNC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3.4 g (9.6 mmol) of 3-(N-tert-butyloxycarbonylaminomethyl)-1-benzhydryl azetidine was dissolved in 170 mL MeOH and hydrogenated over 0.30 g Pd(OH)2 at 5 MPa over night. The catalyst was filtered off and the solvent evaporated. The crude product was purified by flash chromatography using MeOH/CH2Cl2, 1/9, followed by MeOH (saturated with NH3 (g))/CH2Cl2, 1/9, as eluent to yield 1.2 g (67%) of the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(C)(C)OC(=O)NCC1CNC1, amount is: 0.0 ;m1_m2_m3:C(C1=CC=CC=C1)OC(=O)NC(OC)=N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)NCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 0.9 g (4.8 mmol) of 3-(N-tert-butyloxycarbonylaminomethyl) azetidine and 1.3 g (6.3 mmol) of N-benzyloxycarbonyl-O-methylisourea was mixed in 6.5 mL toluene and heated to 70° C. for 72 h and then left at room temperature for another 72 h. Evaporation followed by flash chromatography using EtOAc followed by MeOH (saturated with NH3 (g))/CH2 Cl2, 1/9, as eluent gave 0.67 g (38%) of the title compound as a white powder. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 MOLE;m0_m1_m2:C(C)(C)(C)OC(=O)NCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1, 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(C)(C)(C)OC(=O)NCCC1CN(C1)C(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: The title compound was prepared from 3-aminoethyl-1-benzhydryl azetidine according the procedure for 3-(N-tert-butyloxycarbonylaminomethyl)-1-benzhydryl azetidine, in a yield of 6.5 g (95%). |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C)(C)(C)OC(=O)NCCC1CN(C1)C(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 MOLE;m0_m1_m2:C(C)(C)(C)OC(=O)NCC1CNC1, 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(C)(C)(C)OC(=O)NCCC1CNC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-(N-tert-butyloxycarbonylaminoethyl)-1-benzhydryl azetidine according the procedure for 3-(N-tert-butyloxycarbonylaminomethyl) azetidine, in a yield of 1.2 g (70%). |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C)(C)(C)OC(=O)NCCC1CNC1, amount is: 0.0 MOLE;m0_m1_m2:C(C)(C)(C)OC(=O)NCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=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(C)(C)(C)OC(=O)NCCC1CN(C1)C(NC(=O)OCC1=CC=CC=C1)=N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from 3-(N-tert-butyloxycarbonylaminoethyl) azetidine according the procedure for 3-(N-tert-butyloxycarbonylaminomethyl)-1-(N-benzyloxycarbon ylamidino) azetidine, in a yield of 0.090 g (34%). |
Here is a chemical reaction formula: Reactants are m3:C=1C=C[NH+]=CC1.[O-][Cr](=O)(=O)Cl, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)CCCCO, amount is: 0.0 ;m2:[Cr](=O)(=O)([O-])Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CCOCC, amount is: 0.0 MOLE;m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CCCC=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3.2 mL (20.8 mmol) of 4-phenyl-1-butanol (Aldrich Chemical Co.) in 20 mL of CH2Cl2 at 0° C. was added 3.2 g of powdered 3 Å molecular sieves and then 5.37 g (24.9 mmol) of pyridinum chlorochromate (PCC). The resulting suspension was stirred at 0° C. for 1 h at which time an additional 2.16 g (10.0 mmol) of PCC was added and the reaction mixture was warmed to room temperature. After stirring at ambient temperature for 0.5 h, the reaction mixture was diluted with ether and filtered through celite to give 2.5 g of the crude product. Flash chromatography (elution with 5% ethyl acetate in hexane) yielded 700 mg of the aldehyde 119. 1H NMR was consistent with the structure. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(=CC=CC=C1)CCCC=O, amount is: 0.0 ;m1_m3_m2:C1(=CC=CC=C1)CCC[Mg]Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CCCC(CCCC1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 700 mg (4.7 mmol) of 4-phenyl-1-butanal (119) in 5.0 mL of THF at 0° C. was added 10.0 mL (5.0 mmol) of 3-phenyl-1-propylmagnesium bromide (120) and the resulting mixture was stirred at 0° C. for 0.5 h. The mixture was then quenched by the dropwise addition of saturated NH4Cl and diluted with ether. The phases were separated and the organic layer was washed with water and brine and then dried over MgSO4. Concentration gave 1.12 g of the alcohol 121 as an oil. 1H NMR spectrum was consistent with the structure. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:O(C1=CC=CC=C1)C=1C=C(CO)C=CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(Cl)Cl, amount is: 0.0 ,Catalysts are m1_m2_m3:O=[Mn]=O, amount is: 0.0 ;m4:O=[Mn]=O, amount is: 0.0 .Products are 0:O(C1=CC=CC=C1)C=1C=C(C=O)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1.8mL (10.3 mmol) of 3-phenoxybenzyl alcohol (Aldrich Chemical Co.) in 20 mL of CH2Cl2 at room temperature was added 1.5 g of powdered 4 Å molecular sieves and 2.5 g of activated MnO2. The resulting suspension was stirred at room temperature for 0.5 h, at which time an additional 2.5 g of MnO2 was added. After stirring at room temperature for 0.5 h the reaction mixture was filtered through celite to give 1.84 g of the aldehyde 125 as an oil. 1H NMR consistent with structure. |
Here is a chemical reaction formula: Reactants are m4:C(C)N(CC)CC, amount is: 0.0 ;m1_m5_m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m1_m5_m2:CS(=O)C, amount is: 0.0 ;m3_m6:[Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)/C=C(/CO)\C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:C(Cl)Cl, amount is: 0.0 ;m3_m6:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)/C=C(/C=O)\C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a -78° C. solution of oxalyl chloride (105 μL, 1.2 mmol) in 1.0 mL of methylene chloride was added dimethylsulfoxide (170 μL, 2.4 mmol). The resulting solution was stirred for 5 min and then 170 mg (0.6 mmol) of the alcohol 135 was added in 1.0 mL of methylene chloride. The reaction mixture was stirred at -78° C. for 45 min at which time 500 μL (3.6 mmol) of triethylamine was added and the solution was allowed to warm to ambient temperature. The reaction was quenched with 1.0N HCl and the aqueous layer was extracted with three portions of methylene chloride. The combined organic extracts were dried over MgSO4 and evaporated to dryness to give the crude aldehyde 136 which was used directly in the next reaction. 1H NMR consistent with structure. |
Here is a chemical reaction formula: Reactants are m2_m4_m3:C1(=CC=CC=C1)CCC[Mg]Br, amount is: 0.0 ;m2_m4_m3:C1(=CC=CC=C1)CCCC(CCCC1=CC=CC=C1)O, amount is: 0.0 MOLE;m1:[Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)/C=C(/C=O)\C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m4_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)O[C@@H]1CC[C@H](CC1)\C=C(\C(CCCC1=CC=CC=C1)O)/C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The alcohol 137 was prepared from the crude aldehyde 136. and 1.5 mL (0.75 mmol) of 120 in 2.0 mL of THF as described above for the synthesis of alcohol 121 in Example 1 to give 220 mg of the crude diastereomeric alcohol 137. Flash chromatography (elution with 20% ethyl acetate in hexane) afforded 146 mg of the alcohol 137 as an oil. 1H NMR consistent with structure. |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m3_m4:N1C=C(C2=CC=CC=C12)CCCC(=O)O, amount is: 0.0 ;m1_m5_m2_m3_m4:C(C)(C)N(C(C)C)CC, amount is: 0.0 ;m1_m5_m2_m3_m4:Cl.CN(O)C, amount is: 0.0 ;m1_m5_m2_m3_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 ,this reaction does not need reagents,Solvents are m1_m5_m2_m3_m4:C(C)#N, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CN(C(CCCC1=CNC2=CC=CC=C12)=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a slurry of 1.75 g (8.61 mmol) of 3-indolebutyric acid (Aldrich Chemical Co.) in acetonitrile at room temperature was added 7.0 mL (40.2 mmol) of N,N-diisopropylethylamine, 1.0 g (10.3 mmol) of N,N-dimethylhydroxylamine hydrochloride and 4.19 g (9.5 mmol) of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) and the resulting mixture was allowed to stir at room temperature overnight and was then concentrated to dryness. The residue was dissolved into ethyl acetate and washed with water, 0.5N HCl, saturated NaHCO3 and brine and then dried over MgSO4 and concentrated. Flash chromatography (elution with a gradient of 2-10% ether in methylene chloride) provided 2.0 g of the amide 139. 1H NMR consistent with structure. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CN(C(CCCC1=CNC2=CC=CC=C12)=O)OC, amount is: 0.0 ;m1_m3_m2:C(C1=CC=CC=C1)[Mg]Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)C(CCC(=O)CCC(CC1=CC=CC=C1)C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 147 mg (0.60 mmol) of amide 139 in 4.0 mL of THF at -78° C. was added 1.31 mL (1.31 mmol) of benzylmagnesium chloride (1.0M in Et2O) and the reaction mixture was allowed to warm to room temperature and stir for 3 h. The reaction was quenched with 5% KHSO4 and extracted into ether. The combined ethereal layers were washed with brine and dried over MgSO4. Flash chromatography (elution with 25% ether in hexane) gave 108 mg of the ketone 140. 1H NMR consistent with structure. |
Here is a chemical reaction formula: Reactants are m5:O, amount is: 0.0 MOLE;m2_m6:[Br-].O1C(OCCC1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m3:C(CCC)[Li], amount is: 0.0 ;m4:N1=C(C=CC=C1)C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O1C(OCCC1)C/C=C/C1=NC=CC=C1;0:O1C(OCCC1)C\C=C/C1=NC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 4.6 g (10.2 mmol) of [2-(1,3-dioxan-2yl)ethyl]triphenylphosphonium bromide (Aldrich Chemical Co.) in 50 mL of THF at 0° C. was added 6.4 mL (10.2 mmol) of n-butyl lithium (1.6M in hexanes) and the resulting red solution was allowed to stir at 0° C. for 0.5 h. To this solution was added 880 μL (9.3 mmol) of 2-pyridinecarboxaldehyde (Aldrich Chemical Co.). The reaction mixture was allowed to stir at room temperature for 1 h and was then poured into water and partitioned with ether. The combined either extracts were dried over MgSO4 and concentrated. Flash chromatography (elution with 3:1 hexane:ethyl acetate) gave 0.43 g of E-3-(1,3-dioxan-2-yl)-1-(2-pyridyl)-1-propene (148) and 1.12 g of Z-3-(1,3-dioxan-2-yl)-1-(2-pyridyl)-1-propene (149). 1H NMRs consistent with structures. |
Here is a chemical reaction formula: Reactants are m1_m2:O1C(OCCC1)C\C=C/C1=NC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2:[Pd], amount is: 0.0 .Products are 0:O1C(OCCC1)CCCC1=NC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Through a suspension of 800 mg (4.2 mmol) of olefin 149 and 100 mg of 10% palladium on carbon was bubbled a steady stream of hydrogen gas for a period of 10 min. The reaction mixture was then filtered through celite and concentrated to give 805 mg of the acetal 150 as a colorless oil. 1H NMR consistent with structure. |
Here is a chemical reaction formula: Reactants are m3:C(=O)(O)[O-].[Na+], amount is: 0.0 MOLE;m1_m4:C(=O)(O)C1=CC=C(C=O)C=C1, amount is: 0.0 ;m2:C[Si](C)(C)C=[N+]=[N-], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C1=CC=C(C=C1)C=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 9.6 g (63.6 mmol) of 4-carboxybenzaldehyde (Aldrich Chemical Co.) in 100 mL of CH2Cl2 at 0° C. was added excess trimethylsilyldiazomethane and the resulting mixture was allowed to stir at 0° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated to give 4.3 g of the ester 167 as an oil. 1H NMR consistent with the product. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC(C1=CC=C(C=C1)CCCC1OCCO1)=O, amount is: 0.0 ;m1_m3_m2:[H-].C(C(C)C)[Al+]CC(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O1C(OCCC1)CCCC1=CC=C(C=C1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2.85 g (11.4 mmol) of ester 169 in 25 mL of THF at 0° C. was added 4.4 mL (24.7 mmol) of diisobutylaluminum hydride and the resulting mixture was allowed to stir at 0° C. for 15 min. The reaction was quenched with saturated potassium sodium tartrate and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated to yield 2.58 g of the crude alcohol 170 as an oil. 1H NMR consistent with the product. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:O1C(OCCC1)CCCC1=CC=C(C=C1)CO, amount is: 0.0 ;m1_m2_m4_m3:N1C=NC=C1, amount is: 0.0 ;m1_m2_m4_m3:C(C)(C)(C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)Cl, 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_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC1OCCO1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2.58 g (11.6 mmol) of alcohol 170 and 1.19 g (17.5 mmol) of imidazole in 50 mL of CH2Cl2 was added 3.4 mL (13.1 mmol) of tert-butylchlorodiphenyl silane and the resulting mixture was allowed to stir at room temperature for 1 h. The mixture was then diluted with ethyl acetate and washed with 0.5N HCl. The organic layer was dried over MgSO4, filtered and concentrated. Flash chromatography (elution with 5% ethyl acetate in hexane) afforded 5.5 g of 171. 1H NMR consistent with the product. |
Here is a chemical reaction formula: Reactants are m4_m5:N1C=NC=C1, amount is: 0.0 ;m4_m5:C(C)(C)(C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)Cl, amount is: 0.0 ;m3:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 MOLE;m6:Cl, amount is: 0.0 MOLE;m1_m7_m2:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC1OCCO1, amount is: 0.0 ;m1_m7_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m7_m2:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5.5 g (11.9 mmol) of the dioxolane 171 in 40 mL of THF at room temperature was added 40 mL of 4.0N HCl and the resulting solution was allowed to stir for 1 h. The mixture was neutralized with solid K2CO3, extracted with ethyl acetate and concentrated. The crude mixture was dissolved into 25 mL of CH2Cl2 to which was added 600 mg (8.8 mmol) of imidazole and 1.9 mL (7.3 mmol) of tert-butylchlorodiphenyl silane. The resulting mixture was allowed to stir overnight at room temperature and was then poured into 0.5N HCl and extracted with ethyl acetate. The organics were dried over MgSO4, filtered and concentrated. Flash chromatography (elution with 8% ethyl acetate in hexane) gave 2.12 g of the aldehyde 172 as an oil. 1H NMR consistent with the product. |
Here is a chemical reaction formula: Reactants are m3:C1(=CC=CC=C1)CCCC(CCCC1=CC=CC=C1)O, amount is: 0.0 MOLE;m1_m2_m4:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC=O, amount is: 0.0 ;m1_m2_m4:C1(=CC=CC=C1)CCC[Mg]Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCC1=CC=C(C=C1)CCCC(CCCC1=CC=CC=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The alcohol 173 was prepared from 2.12 g (5.0 mmol) of 172 and 9.0 mL (9 mmol) of 120 in 50 mL of THF as described for the synthesis of 121 in Example 1. Flash chromatography (elution with 10% ethyl acetate in hexane) gave 3.3 g of the alcohol 173. 1H NMR consistent with the product. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m6_m5:I(=O)(=O)(=O)[O-].[Na+], amount is: 0.0 ;m1_m4_m2_m6_m5:CC1N([S@@](OC1)=O)C1=NC=CC=C1, amount is: 0.0 ;m3_m7:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m6_m5:O, amount is: 0.0 ;m1_m4_m2_m6_m5:C(C)#N, amount is: 0.0 ;m3_m7:O, amount is: 0.0 ,Catalysts are m1_m4_m2_m6_m5:[Ru](Cl)(Cl)Cl, amount is: 0.0 .Products are 0:C[C@H]1N(S(OC1)(=O)=O)C1=NC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of sodium periodate (21 g, 0.10 moles) in water (150 ml) was added slowly to a solution of (R)-4-methyl-3-pyridin-2-yl-[1,2,3]oxathiazolidine-2-oxide (15.4 g, 0.78 moles) and ruthenium(III)chloride (20 mg) in acetonitrile (1540 ml) whilst the temperature was kept below 5° C. A heavy precipitate developed. The mixture was poured into a mixture of ethyl acetate (500 ml) and water (500 ml) and then shaken. The organic phase was retained and the aqueous phase was extracted with further ethyl acetate (2×500 ml). The organic phases were combined, backwashed with water (500 ml), dried (MgSO4) and then evaporated in vacuo to give (R)-4-methyl-3-(2-pyridyl)-[1,2,3]oxathiazolidine-2,2-dioxide (15.5 g) as a yellow oil which solidified on standing. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C[C@H]1N(S(OC1)(=O)=O)C1=NC=CC=C1, amount is: 0.0 ;m1_m2_m3:N1(CCNCC1)C1=C2C=CNC2=CC=C1, 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:N1C=CC2=C(C=CC=C12)N1CCN(CC1)C[C@H](NC1=NC=CC=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (R)-4-methyl-3-pyridin-2-yl-[1,2,3]-oxathiazolidine-2,2-dioxide (4.04 g 0.019 moles) and 4-piperazinoindole (3.80 g 0.019 moles) in acetonitrile (200 ml) was heated to 60° C. for 0.5 h then evaporated in vacuo. The residue was taken up into dilute HCl (100 ml), warmed to 60° C. for 0.5 h, cooled, washed with ethyl acetate (2×100 ml), made basic with potassium carbonate, extracted into dichioromethane (3×100 ml), dried (MgSO4) then evaporated in vacuo to give a brown glass. This was purified on a silica column eluting with 10% propan-2-ol in dichloromethane to give (R)-1-(4-indolyl)-4-[2-methyl-2-(2-pyridinylamino)ethyl]piperazine (4.3 g) as a clear glass. |
Here is a chemical reaction formula: Reactants are m3:ClC1=NC=CC=C1, amount is: 0.0 ;m1_m2_m4:NC[C@H](C)O, amount is: 0.0 ;m1_m2_m4:CC(C)([O-])C.[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=C(C=CC=C1)NC[C@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (S)-1-amino-2-propanol (43 g, 0.57M) was added to a stirred solution of potassium tertiary butoxide (64.2 g, 0.66M) in tetrahydrofuran (500 ml). 2-Chloropyridine (65.1 g 0.66M) was then added dropwise. After the exothermic reaction had subsided, the reaction was heated under reflux overnight, filtered to remove the potassium chloride and evaporated to an oil. The crude oil was dissolved in xylene (500 ml) and toluene-p-sulphonic acid (2 g) added and heated overnight under reflux under argon. After cooling to room temperature, the mixture was extracted with 2M hydrochloric acid. The acid extracts were basified with 2M sodium hydroxide and extracted into ethyl acetate. The ethyl acetate extracts were dried (MgSO4) and after removal of the acetic acid the product was distilled affording 73.5 g of the title compound, bp 100°-110° C. at 0.2 mbar. |
Here is a chemical reaction formula: Reactants are m2_m3_m4:NC1=NC=CC=C1, amount is: 0.0 ;m2_m3_m4:C(C)(C)N(CC)C(C)C, amount is: 0.0 ;m1:ClCC(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCC(=O)NC1=NC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Chloroacetylchloride (60 g, 0.53M) was added with stirring to a mixture of 2-aminopyridine (50 g, 0.53M) and diisopropylethylamine (75 ml, 0.53M) in dichloromethane (500 ml) keeping the temperature below 5° C. After the reaction mixture was warmed to room temperature it was filtered and washed with water. The organic layer was dried (MgSO4) and evaporated under reduced pressure to give 72.6 g of a brown solid. |
Here is a chemical reaction formula: Reactants are m2:S(=O)(Cl)Cl, amount is: 0.0 MOLE;m3:N1CCNCC1, amount is: 0.0 MOLE;m1:COC1=C(C=CCO)C=CC=C1, 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:COC1=C(C=CC=C1)/C=C/CN1CCN(CC1)C\C=C\C1=C(C=CC=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Methoxy-cinnamylalcohol (1.44 g) was chlorinated using thionylchloride. Subsequently, reaction with piperazine and other treatments were performed as described in Preparation Example 2, to thereby obtain 314 mg of a salt as colorless prisms. |
Here is a chemical reaction formula: Reactants are m3_m7:BrCC(C(=O)OCC)=O, amount is: 0.0 ;m4:[OH-].[Na+], amount is: 0.0 ;m1_m5_m2_m6:[OH-].[K+], amount is: 0.0 ;m1_m5_m2_m6:C1(C(CCCC1)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:CO, amount is: 0.0 ;m1_m5_m2_m6:CO, amount is: 0.0 ;m1_m5_m2_m6:CO, amount is: 0.0 ;m8:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:O=C1CCCC2=C1C(=CO2)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid was prepared as follows: To a stirred solution of potassium hydroxide (28.06 g, 0.5 mol) in methyl alcohol (100 mL) under nitrogen at 0° C. was added dropwise a solution of cyclohexanedione (56.07 g, 0.5 mol) in methyl alcohol (100 mL). The mixture was stirred at 0° C. for 0.5 h, then a solution of ethyl bromopyruvate (66 mL, 0.525 mol) in methyl alcohol(100 mL) was added dropwise. After allowing the mixture to stir at ambient temperature for 17 h, a 50% aqueous sodium hydroxide solution (60 mL) was added dropwise and stirring continued an additional 7 h. After dilution with water, the solution was acidified and the methanol removed in vacuo. Ice water was added and the precipitate filtered and dried in vacuo to afford 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid. m.p. 137°-138° C. |
Here is a chemical reaction formula: Reactants are m2:C(C)(=O)Cl, amount is: 0.0 ;m1_m3:O=C1CCCC2=C1C(=CO2)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1CCCC2=C1C(=CO2)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred suspension of 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylic acid (28.2 g, 157 mmol) in ethyl alcohol (500 mL) under nitrogen at ambient temperature was added acetyl chloride(56 mL, 783 mmol) dropwise. After stirring 1 h, the solution was then heated at reflux for 1 h. The solution was cooled and concentrated in vacuo. The residue was taken up into dichloromethane, washed with aqueous sodium bicarbonate, washed quickly with 1N sodium hydroxide, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford ethyl 4-oxo-4,5,6,7-tetrahydrobenzofuran-3-carboxylate as an oil. A mixture of this ester (24.46 g, 117 mmol) and ammonium acetate (15.85 g, 206 mmol) in N,N-dimethylformamide (225 mL) was heated at 100° C. under Nitrogen for 1.25 h. The mixture was cooled, poured into ice water, and extracted two times with dichloromethane. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered, concentrated in vacuo, and the residue triturated with ether to give ethyl 4-oxo-4,5,6,7-tetrahydroindole-3-carboxylate. A mixture of this ester (11.31 g, 55 mmol) in 5N sodium hydroxide (200 mL) and ethanol (20 mL) was heated at reflux for 1h. After cooling in an ice bath, the mixture was acidified with concentrated hydrochloric acid, the precipitate filtered, rinsed with ice water, and dried in vacuo to afford 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid. m.p. 269°-270° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3_m5:COC1=C2C=CNC2=CC=C1, amount is: 0.0 ;m1_m2_m4_m3_m5:N1=CC=CC=C1, amount is: 0.0 ;m1_m2_m4_m3_m5:ClC(C(=O)Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3_m5:ClCCl, amount is: 0.0 ;m1_m2_m4_m3_m5:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C2C(=CNC2=CC=C1)C(C(Cl)(Cl)Cl)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-methoxy-1H-indole (7.15 g, 49 mmol) and pyridine (19.7 mL, 243 mmol) in dichloromethane (50 mL) at 0° C. under nitrogen was added dropwise a solution of trichloroacetyl chloride (27.1 mL, 243 mmol) in dichloromethane (50 mL). After stirring at 0° C. for an additional 1.5 h, the mixture was concentrated in vacuo. The residue was taken up in the minimal volume of methanol necessary and placed in a freezer overnight. The precipitate was filtered, rinsed well with methanol, and dried to yield 4-methoxy-3-trichloroacetyl-1H-indole. To a stirring solution of sodium methoxide (3.5 mL of a 25 weight % solution in methanol) in methanol (200 mL) at ambient temperature was added 4-methoxy-3-trichloroacetyl-1H-indole (9.07 g, 31.0 mmol) in portions over 0.75 h. After stirring an additional 0.75 h, the mixture was cooled in an ice bath, diluted with ice water, acidified with concentrated hydrochloric acid, and the methanol removed in vacuo. The resulting heterogeneous mixture was cooled in an ice bath, the precipitate filtered, rinsed with water, and dried to afford methyl 4-methoxy-1H-indole-3carboxylic ester. A slurry of this ester (5.6 g 27 mmol) in 50% aqueous sodium hydroxide (50 mL) and methanol (50 mL) was stirred at ambient temperature for 19 h. The mixture was cooled in an ice bath, acidified with concentrated hydrochloric acid, the precipitate filtered, rinsed with ice water, and dried to afford 4-methoxy-1H-indole-3-carboxylic acid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:BrBr, amount is: 0.0 ;m1_m2_m3_m5:C1(CCCCCC1)=O, amount is: 0.0 ;m1_m2_m3_m5:C(CO)O, amount is: 0.0 ;m4:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:O1CCCC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1COC2(C(CCCCC2)Br)O1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Bromine (44.8 g, 0.28 mol) was added dropwise to a stirred solution of cycloheptanone (28.5 g, 0.25 mol) in a 1:1 solution (300 mL) of ethylene glycol and tetrahydrofuran at room temperature. The mixture was stirred for 5 hours, then poured into aqueous sodium bicarbonate and extracted 3× with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 2-bromocycloheptanone ethylene ketal (60 g). A mixture of this crude bromo ketal and a methanolic solution of sodium methoxide (250 mL, 25 wt. % solution) was heated at reflux overnight. The mixture was cooled to ambient temperature, poured into water, and extracted with hexanes. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 2-cycloheptenone ethylene ketal (39 g). |
Here is a chemical reaction formula: Reactants are m1:O1CCCC1, amount is: 0.0 ;m2:C1COC2(C=CCCCC2)O1, amount is: 0.0 ;m3:[BH4-].[Na+], amount is: 0.0 ;m4:[Cl-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m8:[OH-].[Na+], amount is: 0.0 ;m7_m5:O, amount is: 0.0 ;m6:[OH-].[Na+], amount is: 0.0 ,Catalysts are m7_m5:C(C)(=O)[O-].[Hg+2].C(C)(=O)[O-], amount is: 0.0 .Products are 0:C1COC2(CC(CCCC2)O)O1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mercury(II) acetate (80.7 g, 0.25 mol) was dissolved in water (150 mL), then tetrahydrofuran (150 mL) was added to give a suspension. To this stirring suspension was added 2-cycloheptenone ethylene ketal (39 g, 0.25 mol). After stirring at ambient temperature for 3 hours, the mixture was cooled in an ice water bath. A 10% aqueous sodium hydroxide solution (150 mL) was added, followed by a solution of sodium borohydride (4.8 g, 0.13 mol) in 10% aqueous sodium hydroxide (150 mL). The mixture was allowed to reach ambient temperature and stirred overnight. The mixture was saturated with sodium chloride, stirred for 30 minutes, then allowed to settle; the solution was decanted into brine and extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated in vacuo to give 3-hydroxycycloheptanone ethylene ketal (36 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:O=C1CCCCC=2OC=C(C21)C(=O)OCC, amount is: 0.0 ;m1_m2_m3:C(C)(=O)[O-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1CCCCC=2NC=C(C21)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate (3.48 g, 15.7 mmol) and ammonium acetate (2.41 g, 31.3 mmol) in N,N-dimethylformamide (25 mL) was heated at 115° C. for 6 hours. The mixture was concentrated in vacuo, ice water was added, then extracted 2× with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate then brine, dried over sodium sulfate, filtered through a small pad of Silica gel (1:19 methyl alcohol/dichloromethane), and the filtrate concentrated in vacuo to give ethyl 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylate (1.76 g). A solution of this ester in aqueous 5N sodium hydroxide (30 mL) and ethyl alcohol (6 mL) was heated at reflux for 1 hour, then cooled in an ice bath. The mixture was acidified with hydrochloric acid, and the precipitate collected, rinsed with water followed by diethyl ether and allowed to dry to give 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid (1.17 g). m.p. 225°-227° C. |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 MOLE;m1_m3_m4:O=C1CCCCC=2NC=C(C21)C(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m4:[OH-].[Na+], amount is: 0.0 ;m1_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1CCCCC=2NC=C(C21)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan-3-carboxylate (3.48 g, 15.7 mmol) and ammonium acetate (2.41 g, 31.3 mmol) in N,N-dimethylformamide (25 mL) was heated at 115° C. for 6 hours. The mixture was concentrated in vacuo, ice water was added, then extracted 2× with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate then brine, dried over sodium sulfate, filtered through a small pad of Silica gel (1:19 methyl alcohol/dichloromethane), and the filtrate concentrated in vacuo to give ethyl 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylate (1.76 g). A solution of this ester in aqueous 5N sodium hydroxide (30 mL) and ethyl alcohol (6 mL) was heated at reflux for 1 hour, then cooled in an ice bath. The mixture was acidified with hydrochloric acid, and the precipitate collected, rinsed with water followed by diethyl ether and allowed to dry to give 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid (1.17 g). m.p. 225°-227° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:O=C1N(CCC2=C1C(=CO2)C(=O)OCC)CC, amount is: 0.0 ;m1_m2_m3:C(C)(=O)[O-].[NH4+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C1N(CCC2=C1C(=CN2)C(=O)OCC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl 4-oxo-5-ethyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine-3-carboxylate (3.66 g, 15.4 mmol) and ammonium acetate (5.94 g, 77.1 mmol) in N,N-dimethylformamide (30 mL) was heated at 115° C. for 23 hours. The mixture was cooled, concentrated in vacuo, ice water added, and the precipitate collected and dried to give ethyl 4-oxo-5-ethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-3-carboxylate (1.95 g). The aqueous filtrate was extracted 2× with ethyl acetate, the combined organic layers dried over magnesium sulfate, filtered, and concentrated in vacuo to afford additional ester (0.68 g). The combined materials were treated with aqueous 5N sodium hydroxide (75 mL) in dioxane (10 mL) at reflux for 2 hours. After cooling in an ice water bath, the mixture was acidified with aqueous hydrochloric acid, and concentrated in vacuo. Ethyl acetate was added, the mixture filtered, and the organic layer concentrated in vacuo. Trituration with ethyl acetate afforded 4-oxo-5-ethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid (0.84 g). |
Here is a chemical reaction formula: Reactants are m2_m3:C[O-].[Na+], amount is: 0.0 ;m1:ClC1=NC2=NC(=CC=C2C=C1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=NC2=NC(=CC=C2C=C1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-chloro-7-amino-1,8-napthyridine (Newkome, G. R. et al, J. Org. Chem., 1981, 46, 833-39) (180 mg, 1 mmol) and a methanolic solution of sodium methoxide (458 μL, 25 wt. %) in methyl alcohol (2 mL) was heated at 50° C. for 19 hours. The reaction mixture was allowed to cool, filtered through Celite using dichloromethane, concentrated in vacuo and the residue purified on Silica gel (1:9:0.2 methyl alcohol/dichloromethane/ammonium hydroxide) to afford 2-methoxy-7-amino-1,8-naphthyridine as a pale yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m6_m3:O=C1C=2C(=CNC2CCC1)C(=O)O, amount is: 0.0 ;m1_m2_m6_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m6_m3:ClC(=O)OCC, amount is: 0.0 ;m5:[Cl-].[NH4+], amount is: 0.0 MOLE;m4_m7:COC1=NC=C(C=C1)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m6_m3:CN(C=O)C, amount is: 0.0 ;m4_m7:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=C(C=NC=C1)NC(=O)C1=CNC=2CCCC(C12)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirring solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (179 mg, 1 mmol) and triethylamine (293 μl, 2.1 mmol) in N,N-dimethylformamide (3 mL) at 0° C. was added ethyl chloroformate (191 μl, 2 mmol). After stirring an additional 30 minutes, a solution of 2-methoxy-5-amino-pyridine (216 mg, 2 mmol) in N,N-dimethylformamide (3 mL) was added. The reaction mixture was allowed to stir for an additional 75 minutes, then poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers were washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. To the residue was added aqueous 5N sodium hydroxide (5 mL) and ethyl alcohol (1 mL), then heated at reflux for 1 hour. After cooling in an ice water bath, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, concentrated in vacuo, and the residue recrystallized from ethyl acetate to give N-(4-methoxy-3-pyridyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole 3-carboxamide (56 mg); m.p. 209°-210° C. (Compound 1). |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1, amount is: 0.04800000041723251 MOLE;m1_m3_m2_m4:C=1C=CC=2C(C1)=CC(=C(C2CC3=C4C=CC=CC4=CC(=C3O)C(=O)O)O)C(=O)O, amount is: 0.04800000041723251 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C(C)O, amount is: 0.0 ;m1_m3_m2_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=C(C(=CC2=CC=CC=C12)C(=O)O)O)C1=C(C(=CC2=CC=CC=C12)C(=O)O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C(N=C3N(C2=O)CCCC3)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.048mol) in ethanol (600ml) was added to a solution of pamoic acid (0.048mol) in N,N-dimethylformamide (400ml). The mixture was stirred for 3 hours. The resulting precipitate was filtered off by suction, washed with ethanol and dried, yielding 31 g (81%) of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 4,4'-methylenebis[3-hydroxy-2-naphthalenecarboxylate](1:1); mp. 269.2° C. |
Here is a chemical reaction formula: Reactants are m1:COC1=C(C=NC=C1)[N+](=O)[O-], amount is: 0.0 ;m2_m5:CN, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:CCO, amount is: 0.0 MOLE;m2_m5:CCO, amount is: 0.0 ;m3:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CNC1=C(C=NC=C1)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Methoxy-3-nitropyridine (8.17 g, 53.0 mmol) was transferred to a bomb in EtOH (5-10 mL). To this was added a solution of methylamine in EtOH (26.4 mL, 8.03M, 0.212 mol). The bomb was sealed and lowered into an oil bath at 120° C. The bath temperature fell to 90° C. and remained that way for 2 hours. The temperature was raised to 140° C. over 0.5 hour and held there 0.5 hour. The contents were transferred to a flask with EtOH (not very soluble) and the solvent was evaporated. Flash chromatography on silica gel with a gradient of CH2Cl2 /CH3OH gave 7.17 g (88%) of 4-methylamino-3-nitropyridine as a yellow solid: mp 155°-158° C. |
Here is a chemical reaction formula: Reactants are m1_m2:NC=1C(=NC=CC1NC)Cl, amount is: 0.0 ;m1_m2:C(OCC)(OCC)OCC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m3:OS(=O)(=O)O, amount is: 0.0 MOLE.Products are 0:ClC1=NC=CC2=C1N=CN2C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a heterogeneous mixture of 3-amino-2-chloro-4-methylaminopyridine (5.9 g, 37 mmol) and triethyl orthoformate (12.92 mL, 87.2 mmol) was added 5 drops of conc. H2SO4. A short path distillation apparatus was attached. The reaction flask was lowered into a hot oil bath and stirred at 110° C. to 190° C. The time spent heating was 20-25 minutes. On cooling, the thick residue was dissolved in CH2Cl2 (40 mL) and was allowed to stir overnight with a little CaO. The solid was removed by filtration and the filtrate was concentrated. Flash chromatography on silica gel eluting with (CH2Cl2 /CH3OH, 95:5) gave 5.65 g (91%) of 4-chloro-1-methyl-1H-imidazo[4,5-c]pyridine as a light yellow solid: mp 127°-131° C.; MS 167 (M+). |
Here is a chemical reaction formula: Reactants are m2:C(C)N1CC(CCC1)=O, amount is: 0.0 ;m1:C(C1=CC=CC=C1)N1C=NC=2C(=NC=CC21)Cl, 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)N1C(=NC=2C(=NC=CC21)Cl)C2(CN(CCC2)CC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the procedure of Example 13 and using 1-benzyl-4-chloro-1H-imidazo[4,5-c]pyridine (0.60 g, 2.5 mmol) and (0.36 g, 2.8 mmol) of N-ethyl-3-piperidone gave the free base of the title compound which was purified by flash chromatography on silica gel eluting with EtOAc to give, after preparation of the salt, the dihydrochloride, 0.59 hydrate as an amorphous solid, 0.30 g (26%): |
Here is a chemical reaction formula: Reactants are m3_m5:FC(CO)(F)F, amount is: 0.0 ;m1_m2_m4:ClC1=NC(=NC=C1)SC, amount is: 0.0 ;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 MOLE;m3_m5:CN(C)C=O, amount is: 0.0 ;m1_m2_m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CSC1=NC=CC(=N1)OCC(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-chloro-2-methylthiopyrimidine (16.0 g) and potassium carbonate (27.6 g) in DMF (90 ml) at 0° C., was added with stirring a solution of 2,2,2-trifluoroethanol (10.0 g) in DMF (10 ml). Stirring was continued for 64 hours, then the reaction mixture was diluted with water and extracted with ether (3×150 ml). The combined extracts were washed with brine, dried and concentrated to give 2-methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine (23.0 g, crude yield) as a clear pale orange oil, 1H NMR δ 2.57(3H,s); 4.79(2H,q); 6.54(1H,d); 8.33(1H,d) ppm. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m5:CSC1=NC=CC(=N1)OCC(F)(F)F, amount is: 0.0 ;m1_m4_m2_m5:[Mn](=O)(=O)(=O)[O-].[K+], amount is: 0.0 ;m1_m4_m2_m5:C(C)(=O)O, amount is: 0.0 ;m3:S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CS(=O)(=O)C1=NC=CC(=N1)OCC(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine (1.0 g) in glacial acetic acid (20 ml) at 15° C. was added a solution of potassium permanganate (2.4 g) in water (75 ml). When the addition was complete a solution of sodium metabisulphite (10% aqueous) was added until a clear solution was obtained. The reaction mixture was extracted with ether (3×70 ml), the combined extracts were washed with brine (3×), dried and concentrated to give 2-methanesulphonyl-4-(2,2,2-trifluorethoxy)-pyrimidine (1.0 g, 87% yield) as a clear oil; 1H NMR δ 3.35(3H,s); 4.91(2H,q); 7.11(1H.d); 8.69(1H,d) ppm. |
Here is a chemical reaction formula: Reactants are m4_m5:C1(CCCC1)Br, amount is: 0.0 ;m4_m5:C([O-])([O-])=O.[Cs+].[Cs+], amount is: 0.0 ;m1_m2_m3_m6:C([O-])([O-])=O.[Cs+].[Cs+], amount is: 0.0 ;m1_m2_m3_m6:OC=1C=C(C=O)C=CC1OC, amount is: 0.0 ;m1_m2_m3_m6:C1(CCCC1)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m6:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=O)C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Caesium carbonate (214 g, 0.66 mol) was added to a mixture of 3-hydroxy-4-methoxybenzaldehyde (100 g, 0.66 mol) and cyclopentyl bromide (98 g, 0.66 mol) in anhydrous DMF (50 ml). The reaction mixture was stirred at RT for 16 h then treated with a further portion of cyclopentyl bromide (98 g, 0.66 mol) and caesium carbonate (214 g, 0.66 mol). After a further 6 h at RT, the mixture was filtered and concentrated in vacuo. The residue was dissolved in dichloromethane (300 ml) and washed with sodium hydroxide solution (10%; 2×150 ml). The organic layer was dried (MgSO4), concentrated in vacuo, and distilled (150° C., 10-2 mbar) to afford the title compound (130 g) as a viscous colourless oil. (Found: C, 70.38; H, 7.48. C13H16O3 requires C, 70.89; H 7.32%); δH (CDCl3) 1.5-2.0 (8H, br m, CH2)4), 3.87 (3H, s, OMe), 4.80 (1H, br m, OCHCH2), 6.90 (1H, d, J 8.7 Hz. ArH ortho to OMe), 7.30-7.45 (2H, m. 2×ArH meta to OMe), and 9.77 (1 H, s, ArCHO). |
Here is a chemical reaction formula: Reactants are m3:IC, amount is: 0.0 ;m1_m5_m2_m6:ClC=1C=NC=C(C1)Cl, amount is: 0.0 ;m1_m5_m2_m6:[Li+].CC(C)[N-]C(C)C, amount is: 0.0 ;m4_m7:C(O)([O-])=O.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2_m6:C1CCOC1, amount is: 0.0 ;m1_m5_m2_m6:C1CCOC1, amount is: 0.0 ;m4_m7:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=NC=C(C1C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3,5-Dichloropyridine (2.04 g, 13.5 mmol) in THF (5 ml) was added dropwise to a solution of LDA [prepared from diisopropylamine (1.9 ml, 13.5 mmol) and n-butyllithium (1.6M, 8.4 ml, 13.5 mmol)] in THF (25 ml) at -70° C. After stirring at this temperature for 5 min, iodomethane (0.85 ml, 13.5 mmol) was added and the reaction mixture stirred for a further 1.5 h at -70° C. Saturated sodium hydrogen carbonate solution (20 ml) and dichloromethane (20 ml) was added and the organic phase separated, dried (MgSO4), and concentrated in vacuo. The residue was subjected to chromatography (SiO2 ; Et2O-hexane, 1:3) to afford the title compound (1.16 g) as a pale yellow solid; δH (CDCl3) 2.46 (3H, s, Me), and 8.36 (2H, s, pyridine H2, H6). |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3_m5:[O-]CC.[Na+], amount is: 0.0 ;m1_m4_m2_m3_m5:N1=CC=C(C=C1)C=O, amount is: 0.0 ;m1_m4_m2_m3_m5:[Cl-].C1(CCCC1)OC=1C=C(C=CC1OC)C1=C(C=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3_m5:C(C)O, amount is: 0.0 ;m1_m4_m2_m3_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)\C=C/C1=CC=NC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of sodium ethoxide [prepared from sodium (0.10 g, 4.50 mmol)] in ethanol (50 ml) was added over 5 min to a stirred mixture of 4-pyridine carboxaldehyde (0.44 g, 4.10 mmol) and (3-cyclopentyloxy-4-methoxyphenyl)-methyltriphenylphosphonium chloride (2.00 g, 4.08 g) in ethanol (30 ml). After 2h, the reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc (75 ml) and brine (50 ml). The organic layer was separated, then dried (MgSO4) and concentrated in vacuo. A 1H n.m.r. spectrum indicated that the mixture consisted of a 3:2 mixture of (Z): (E)title compound (and triphenylphosphine oxide). A portion (0.6 g) of the mixture was subjected to chromatography (SiO2 ; hexane to EtOAc) to afford pure/Z-title compound (0.14 g) as a pale yellow solid m.p. (Found: C, 77.18; H, 7.16; N, 4.63. C19H21NO2 requires C, 77.26; H, 7.17; N, 4.74%); δH (300 MHz; CDCl3) 1.5-1.55 (2H, br m, cyclopentyl H's), 1.65-1.9 (6H, br m, cyclopentyl H's), 3.83 (3H, s, OMe), 4.44 (1H, br m, OCHCH2), 6.40 (1H, d, J 12.2 Hz, CH=CH), 6.65-6.80 (4H, m, ArH ortho to OMe+2×ArH meta to OMe+CH=CH), 7.15 (2H, ca. d, J 6.0 Hz, pyridine H2, H6); m/z 295 (M+, 22%), 228 (15), 227 (100), 226 (94), 198 (35), 184 (15), 166 (12), 43 (19), and 41 (29). |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)(=O)[O-].[NH4+], amount is: 0.0 ;m1_m2:C(#N)[BH3-].[Na+], amount is: 0.0 ;m3:ClC1=CC=C(OC(C(C)=O)C)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC=C(OC(C(C)N)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 82 g of ammonium acetate and 6.7 g of sodium cyanoborohydride were added to a solution containing 21 g of 3-(4-chlorophenoxy)-2-butanone dissolved in 500 mL of methanol, and the reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was then concentrated under reduced pressure, and 180 mL of concentrated hydrochloric acid and 100 mL of water were added to the residue. The whole mixture was extracted with 300 mL of diethyl ether. The obtained water layer was alkalifled using a 5% aqueous solution of sodium hydroxide, and then extracted with 500 mL of ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. A fraction possessing a low boiling point was removed from the obtained oily products to afford 18 g (yield 86%) of the desired product. Refractive index: 1.5360. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:NC(CO)C, amount is: 0.0 ;m1_m2_m4:[H-].[Na+], amount is: 0.0 ;m3:Cl.ClC1=CC=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(COC1=CC=NC=C1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 6.2 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 4.0 g of 60% sodium hydride and 50 mL of N,N-dimethylformamide at 5° C.-10° C. After the reaction mixture was stirred for 30 minutes, 12.5 g of 4-chloropyridine hydrochloride in limited amounts was added to the reaction mixture. The mixture was stirred for 20 hours at room temperature. After completion of the reaction, the solids were filtered off. The solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 3.8 g of the desired product (yield: 30%). Refractive index: 1.5469. |
Here is a chemical reaction formula: Reactants are m2:N#N.C(C)(C)(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(COC1=CC=C(C=C1)C#N)C, amount is: 0.0 ;m1:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(#N)C1=CC=C(OCC(C)NC([C@@H](N)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Hydrogen chloride gas was introduced into a solution containing 3.7 g of N2 -tert-butoxycarbonyl-N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide dissolved in 100 mL of methylene chloride for 1 hour at room temperature. After completion of the reaction, the methylene chloride was removed under reduced pressure, thus obtaining a crude crystal. The crude crystal was washed with acetone to afford 3.1 g of the desired product (yield: 100%). Melting point: 59°-63° C. |
Here is a chemical reaction formula: Reactants are m1:CN1CCCCC1, amount is: 0.0 ;m4:C(#N)C1=CC=C(OCC(C)N)C=C1, amount is: 0.0 ;m3:ClC(=O)OCC(C)C, amount is: 0.0 ;m2:O(C1=CC=CC=C1)C(=O)N[C@@H](C(C)C)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(Cl)Cl, amount is: 0.0 ;m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(#N)C1=CC=C(OCC(C)NC([C@@H](NC(=O)OC2=CC=CC=C2)C(C)C)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.8 g of N-methylpiperidine was added to a solution containing 4.2 g of N-phenoxycarbonyl-L-valine dissolved in 100 ml of methylene chloride, at -20° C. After the mixture was stirred for 10 minutes at the same temperature. 2.4 g of isobutyl chloroformate was added to the mixture, and stirred for 1 hour at -20° C. 3.1 g of 2-(4-cyanophenoxy)-1-methylethylamine was added to this mixture at -60° C., and then the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and was stirred for 20 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed successively with a 5% aqueous solution of sodium bicarbonate and water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus obtaining 1.0 g of a white powder. 0.6 g of the obtained white powder was purified using high pressure liquid chromatography (hereinafter, referred to as "HPLC") (YMC-063-15, hexane/ethyl acetate=55/45) to separate two fractions. The ingredient of the first fraction possessing a short retention time was 0.3 g of a white powder (yield: 7%) possessing 145 to 147° C. of melting point and the ingredient of the second fraction possessing a long retention time was 0.3 g of a white powder (yield: 7%) possessing a melting point of 166° to 170° C. of melting point. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)(=O)C1=NC=CC2=CC=CC=C12, amount is: 0.0 ;m1_m2_m3_m4:NO, amount is: 0.0 ;m1_m2_m3_m4:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m1_m2_m3_m4:CO, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE;m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C1=NC=CC2=CC=CC=C12)=NO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1-acetyl-isoquinoline (3.42 g), hydroxylamine (1.53 g) and sodium acetate (2.46 g) in a 3:1 mixture of methanol:water (80 ml) was heated to reflux for 8 hours then allowed to stand for 16 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The combined extracts were dried, concentrated and chromatographed using ethyl acetate:hexane 3:7 as the eluant to give 1-acetyl-isoquinoline oxime (1.87 g, 58% yield) as a white crystalline solid m.p. 154.4°-155.3° C.; 1H NMR: 2.50(3H,s); 7.58-7.73(3H,m); 7.85(1H,m); 8.55(1H,m); 8.57(1H,m); 8.66(1H,s) ppm. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:C(C)(=O)C=1N=CC2=CC=CC=C2C1, amount is: 0.0 ;m1_m2_m3_m4_m5:NO, amount is: 0.0 ;m1_m2_m3_m4_m5:C(C)(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 MOLE;m1_m2_m3_m4_m5:CO, amount is: 0.0 ;m1_m2_m3_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C=1N=CC2=CC=CC=C2C1)=NO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-acetyl-isoquinoline (0.65 g), hydroxylamine (0.29 g) and sodium acetate (0.47 g) in a mixture of methanol (20 ml) and water (3 ml) was heated to reflux for 1.5 hours. The reaction was then poured into water and extracted with ethyl acetate. The combined extracts were dried, concentrated and triturated with hexane to give 3-acetyl-isoquinoline oxime (0.63, 89% yield) as a white crystalline solid m.p. 135°-142° C.; 1H NMR: 2.50(3H,s); 7.61(1H,t); 7.70(1H,t); 7.87(1H,d); 7.99(1H,d); 8.11(1H,s); 9.28(1H,s) ppm. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4_m5:C(C)(=O)C1=NC=CC(=N1)C1=NC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4_m5:NO, amount is: 0.0 ;m1_m2_m3_m4_m5:C(C)(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4_m5:C(C)O, amount is: 0.0 ;m1_m2_m3_m4_m5:O, amount is: 0.0 ;m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(C1=NC=CC(=N1)C1=NC=CC=C1)=NO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-acetyl-4-(pyrid-2-yl)-pyrimidine (1.0 g), hydroxylamine (0.39 g) and sodium acetate (0.62 g) in a mixture of ethanol (10 ml) and water (2 ml) was heated to reflux for 1.5 hours. The reaction was then poured into water the precipitate filtered and washed with hexane to give 2-acetyl-4-(pyrid-2-yl)-pyrimidine oxime (0.98 g, 91% yield) as a white crystalline solid m.p. 196°-8° C.; 1H NMR: 2.50(3H,s); 7.42(1H,m); 7.88(1H,m); 8.30(1H,d); 8.59(1H,d); 8.74(1H,d); 8.90(1H,d); 10.85(1H,brs) ppm. |
Here is a chemical reaction formula: Reactants are m3:O, amount is: 0.0 MOLE;m1_m2:C(C)OC(=O)N1C[C@H]([C@H](CC1)NC(C1=C(C=C(C(=C1)Cl)N)O[C@H](C#CC)C)=O)OC, amount is: 0.0 ;m1_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CC(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CO[C@@H]1CNCC[C@@H]1NC(C1=C(C=C(C(=C1)Cl)N)O[C@H](C#CC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.50 g of the cis-N-(1-ethoxycarbonyl-3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide prepared in the Example 7 and 4.5 g of potassium hydroxide were dissolved in 2-propanol. The obtained solution was refluxed for 1.5 hours and cooled, followed by the addition thereto of water. The resulting mixture was extracted with 10% 2-propanol/chloroform thrice. The combined organic phases were dried over magnesium sulfate and freed from the solvent. The residue was purified by silica gel column chromatography (5 to 12% methanol/dichloromethane) to give 0.34 g of the title compound. |
Here is a chemical reaction formula: Reactants are m4:CN(C)C=O, amount is: 0.0 ;m3:C(C)N(CC)CC, amount is: 0.0 ;m2:FC1=CC=C(OCCCBr)C=C1, amount is: 0.0 ;m1:CO[C@@H]1CNCC[C@@H]1NC(C1=C(C=C(C(=C1)Cl)N)O[C@H](C#CC)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC=C(OCCCN2C[C@H]([C@H](CC2)NC(C2=C(C=C(C(=C2)Cl)N)O[C@H](C#CC)C)=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture comprising 0.10 g of the cis-N-(3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide, 0.07 g of 3-(4-fluorophenoxy)propyl bromide, 0.20 g of triethylamine and 10 ml of DMF was stirred at 50° C. for 2 hours and cooled. Ethyl acetate was poured into the resulting mixture. The obtained mixture was washed with water thrice, dried over magnesium sulfate, and freed from the solvent. The residue was purified by silica gel column chromatography (5% methanol/dichloromethane) to give 0.13 g of the title compound. |
Here is a chemical reaction formula: Reactants are m4:ON1N=NC2=C1C=CC=C2, amount is: 0.0 MOLE;m1_m2:NC1=CC(=C(C(=O)O)C=C1Cl)O[C@H](C#CC)C, amount is: 0.0 ;m1_m2:NC1N2CC(CC1CC2)CC2=CC=CC=C2, amount is: 0.0 ;m3:CCN=C=NCCCN(C)C.Cl, 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(C1=CC=CC=C1)N1CC2CCC(C1)C2NC(C2=C(C=C(C(=C2)Cl)N)O[C@H](C#CC)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The condensation of 530 mg of (S)-4-amino-5-chloro-2-[(1-methyl-2-butynyl)oxy]benzoic acid with 850 mg of 8-amino-3-benzylazabicyclo[3.2.1]octane was conducted in a similar manner to that of the Example 34 by the use of WSC.HCl and 1-hydroxybenzotriazole (HOBT). The product was purified by silica gel column chromatography (5% methanol/chloroform) to give 220 mg of the title compound. |
Here is a chemical reaction formula: Reactants are m4:BrC(C(CC=O)(F)Cl)(F)F, amount is: 0.0 MOLE;m5:Cl(=O)[O-].[Na+].OO, amount is: 0.0 MOLE;m1_m2_m3:ClC(C(Br)(F)F)(Br)F, amount is: 0.0 MOLE;m1_m2_m3:C(=C)OCC, amount is: 0.0 MOLE;m1_m2_m3:S(=O)([O-])S(=O)[O-].[Na+].[Na+].C([O-])(O)=O.[Na+], 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(C(CC(=O)O)(F)Cl)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A one pot reaction of 1-chloro-1,2-dibromotrifluoroethane (VI) with ethyl vinyl ether in the presence of sodium hydrosulfite/sodium bicarbonate followed by oxidation of the intermediate, 4-bromo-3-chloro-3,4,4-trifluorobutanal (VII), without isolaton, with sodium chlorite/hydrogen peroxide to give 4-bromo-3-chloro-3,4,4-trifiuorobutanoic acid (VIII) in overall unexpected yields; |
Here is a chemical reaction formula: Reactants are m1:BrC(C(CC(=O)O)(F)Cl)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m2:[Zn], amount is: 0.0 MOLE.Products are 0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dehalogenation of 4-bromo-3-chloro-3,4,4-trifluorobutanoic acid (VIII) with zinc using conditions analogous to those disclosed in the literature to obtain the desired 3,4,4-trifluoro-3-butenoic acid (IV); or |
Here is a chemical reaction formula: Reactants are m2_m3_m4_m5_m6:ClC(C(Br)(F)F)(Br)F, amount is: 0.0 MOLE;m2_m3_m4_m5_m6:ClC(C(Cl)(F)F)(Cl)F, amount is: 0.0 MOLE;m2_m3_m4_m5_m6:C(=C)(Cl)Cl, amount is: 0.0 MOLE;m2_m3_m4_m5_m6:S(=O)(=O)([O-])OOS(=O)(=O)[O-].C(=O)[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m4_m5_m6:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:BrC(C(CC(=O)O)(F)Cl)(F)F;0:ClC(CC(=O)O)(C(F)(F)Cl)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A one pot reaction of 1-chloro-1,2-dibromotrifluoroethane (VI) or 1,1,2-trichlorotrifiuoroethane (X) with vinylidene chloride in the presence of ammoninm persulfate/sodium formate/air in DMF to give 4-bromo-3-chloro-3,4,4-trifiuorobutanoic acid (VIII) or 3,4- dichloro-3,4,4-trifluorobutanoic acid (XI). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:FC(CC(=O)O)=C(F)F, amount is: 0.0 MOLE;m1_m2_m3:C(C(=O)Cl)(=O)Cl, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:CN(C)C=O, amount is: 0.0 MOLE.Products are 0:FC(CC(=O)Cl)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Reaction of 3,4,4-trifiuoro-3-butenoic acid (IV) with oxalyl chloride in the presence of DMF as a catalyst without any solvent to give 3,4,4-trifluoro-3-butenoyl chloride (V). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC(CCO)=C(F)F, amount is: 0.0 MOLE;m1_m3_m2:CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2:CC(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The first method involves hydrolysis of 4-bromo-1,1,2-trifluoro-1-butene (II) with water in the presence of N-methyl pyrrolidinone to give 3,4,4-trifiuoro-3-buten-1-ol (III), followed by Jones oxidation under conditions not previously known. These conditions are at a temperature of about 51°-54° C. In addition, the 3,4,4-trifluoro-3-buten-1-ol in acetone solvent and the Jones reagent are added to the reaction vessel simultaneously to afford 3,4,4-trifluoro-3-butenoic (IV) acid in 52% overall yield. ##STR4## |
Here is a chemical reaction formula: Reactants are m1:BrC(C(CC(=O)O)(F)Cl)(F)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m2:[Zn], amount is: 0.0 MOLE.Products are 0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In the second method the synthesis of 4-bromo-3-chloro-3,4,4-trifiuoro-butanoic acid (VIII) is followed by zinc dehalogenation to produce 3,4,4-trifiuoro-3-butenoic acid (IV). This compound is prepared by reacting 1-chloro-1,2-dibromotrifiuoroethane (VI) with ethyl vinyl ether in the presence of sodium dithionite and sodium bicarbonate in a manner analogous to that described in the Literature [Huang, Weiyuan; lu, long; Zhang, Yuanfa; Chin. J. Chem. 1990, (3), 281]. However, it is now found that the 4-bromo-3-chloro-3,4,4-trifluorobutanal intermediate (VII) is oxidized without isolation with sodium chlorite/hydrogen peroxide. In other words, instead of oxidation with Jones reagent, this method advantageously provides a process which can be carried out in one reaction vessel using preferred reagents and gives an unexpectedly high yield. |
Here is a chemical reaction formula: Reactants are m2_m3_m4_m5_m6_m8:ClC(C(Cl)(F)F)(Cl)F, amount is: 0.0 ;m2_m3_m4_m5_m6_m8:C(=C)(Cl)Cl, amount is: 0.0 ;m2_m3_m4_m5_m6_m8:S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+], amount is: 0.0 ;m2_m3_m4_m5_m6_m8:C(=O)[O-].[Na+], amount is: 0.0 ;m2_m3_m4_m5_m6_m8:O, amount is: 0.0 ;m7:C(=O)=O.CC(=O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m4_m5_m6_m8:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC(CC(=O)O)(C(F)(F)Cl)F;0:FC(CC(=O)O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1,1,2-trichlorotrifluoroethane (X) (9.37 g, 50 mmol), vinylidene chloride (4.85 g, 50 mmol), ammonium persulfate (11.41 g, 50 mmol), sodium formate (3.4 g, 50 mmol) and water (1.8 g, 0.1 mol) in DMF (80 mL) was stirred (dry-ice/acetone condensor) at room temperature with air bubbling. After 30 min, an aliquot of the reaction mixture was acidified with dilute HCl, extracted with ether and analyzed by GC, which indicated the formation of two products. These products were identified by GC/MS (EI) as 4-chloro-3,4,4-trifluoro-2-butenoic acid and novel compound 3,4-dichloro-3,4,4-trifluorobutanoic acid (XI). The compound XI gives 3,4,4-trifluoro-3-butenoic acid (IV) upon reaction with zinc. Under the above reaction conditions, 1-chloro-1,2-dibromotrifluoroethane (VI) gave 3-chloro-4-bromo-3,4,4-trifluorobutanoic acid (VIII) as one of the products. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N1N=CN=C1, amount is: 0.0 ;m1_m3_m2:FC(CC(=O)Cl)=C(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(CC(=O)N1N=CN=C1)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 1,2,4-triazole (1.38 g, 20 mmol) in ethyl acetate (100 mL) was added 3,4,4-trifluoro-3-butenoyl chloride (1.59 g, 10 mmol) at r.t. with stirring. The mixture was stirred for 30 min and filtered. The residue obtained after evaporation of the solvent was redissolved in dichloromethane (25 mL) and filtered. Evaporation of the solvent gave 1.8 g (94%) of the desired product as a dear oil. |
Here is a chemical reaction formula: Reactants are m2_m3:FC(CBr)=C(F)F, amount is: 0.0 ;m2_m3:P(OCC)(OCC)OCC, 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:FC(C(=C)F)(F)P(OCC)(OCC)=O;0:FC(CP(OCC)(OCC)=O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2,3,3-trifluoro-2-propenyl bromide (5.25 g, 30 mmol) and triethyl phosphite (4.15 g, 25 mmol) in acetonltrile (15 mL) was heated at reflux for overnight. The residue obtained after evaporation of the solvent was chromatographed over silica gel (hexanes/ethyl acetate/ethanol, 80/20/1) to give diethyl (1,1,2-trifluro-2-propenyl)phosphonate (0.8 g, 11%) and diethyl (2,3,3-trifluro-2-propenyl)phosphonate (1.0 g, 14%). |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 MOLE;m1_m3:FC(CP(OC(C)(C)C)(OC(C)(C)C)=O)=C(F)F, 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:FC(CP(O)(O)=O)=C(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The above di-t-butylphosphonate (0.5 g) was dissolved in 3 mL of methanol and treated with 0.5 mL, of 3N HCl and allowed to stand at r.t. for 30 min. The solution was concentrated and the residue was redissolved in 10 mL of water and washed with 10 mL of ether. Evaporation of the aqueous layer gave 0.14 g of 2,3,3-trifluoro-2-propenylphosphonic acid as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m2:CO, amount is: 0.0 ;m1_m2:O(C1=CC=CC=C1)C1=CC=C(C=C1)C=1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:C(C)(=O)O, amount is: 0.0 ,Catalysts are m3_m4:[C].[Pd], amount is: 0.0 .Products are 0:O(C1=CC=CC=C1)C1=CC=C(C=C1)C1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a 100 ml methanol solution of 3.51 g of the compound (3) synthesized in Reference Example 3 were added 200 mg of palladium carbon and 1 ml of acetic acid for hydrogenation at atmospheric pressure and room temperature. After the end of the reaction, the insolubles were filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in methylene chloride, then adjusted by a 10% aqueous solution of sodium hydroxide to pH=9 to 10, then was shaken. The organic layer was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol=20:1!) to obtain the above-reference compound (4) in all amount of 2.32 g (yield of 66%). |
Here is a chemical reaction formula: Reactants are m1_m2:FC1=CC=C(C=C1)CC1=CC=C(N)C=C1, amount is: 0.0 ;m1_m2:Cl.ClCCNCCCl, 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=C1)CC1=CC=C(C=C1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 500 mg of 4-(4-fluorophenyl) methylaniline and 445 mg of bis(2-chloroethyl)amine hydrochloride was stirred at 100° C. for 2 hours, then gradually raised in temperature to 200° C. and then further stirred for 2 hours. This was then cooled to room temperature, then the product was purified by silica gel column chromatography (chloroform:methanol:water (2% acetic acid)=65:35:5) to obtain the above-referenced compound (5) in an amount of 503 mg (yield of 75%). |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m3:B(OC(C)C)(OC(C)C)OC(C)C, amount is: 0.0 ;m1_m5_m2:COC=1C=CC2=C(SC=C2)C1, amount is: 0.0 ;m1_m5_m2:C(CCC)[Li], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(C)(=O)OCC, amount is: 0.0 ;m1_m5_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=CC2=C(SC(=C2)B(O)O)C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 6-methoxybenzo[b]thiophene (18.13 g, 0.111 mol) in 150 mL of anhydrous tetrahydrofuran (THF) at -60° C. was added n-butyllithium (76.2 mL, 0.122 mol, 1.6M solution in hexanes), dropwise via syringe. After stirring for 30 minutes, triisopropyl borate (28.2 mL, 0.122 mol) was introduced via syringe. The resulting mixture was allowed to gradually warm to 0° C. and then distributed between 1N hydrochloric acid and ethyl acetate (300 mL each). The layers were separated, and the organic layer was dried over sodium sulfate. Concentration in vacuo produced a white solid that was triturated from ethyl ether hexanes. Filtration provided 16.4 g (71%) of 6-methoxybenzo[b]thiophene-2-boronic acid as a white solid. mp 200° C. (dec). 1H NMR (DMSO-d6) d 7.83 (s, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.51 (d, J=2.0 Hz, 1H), 6.97 (dd, J=8.6, 2.0 Hz, 1H), 3.82 (s, 3H). FD mass spec: 208. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:C(=O)(O)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)O, amount is: 0.0 ;m1_m4_m2:S(=O)(Cl)Cl, amount is: 0.0 ;m3:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C1=C(C=C(C=C1)[N+](=O)[O-])S(=O)(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 190.0 g (0.77 mol) of 2-carboxy-5-nitrobenzenesulfonic acid, 10 ml of DMF and 250 ml (3.43 mol) of thionyl chloride is heated at boiling for 3 h. After separating off the insoluble constituents by filtration, the filtrate is concentrated. 200 ml (4.94 mol) of methanol are added to the residue which results. When addition is complete the reaction mixture is cooled to 0° C. The solid which precipitates is filtered off and dried. 70.9 g (35.3% of theory) of colorless, crystalline 2-methoxycarbonyl-5-nitrobenzenesulfonic acid (m.p.: 92°-94° C.) are thus obtained. By distilling off the volatile components from the mother liquor, a second fraction (62.5 g, 31.1% of theory) is obtained. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)NC)C(=O)OC, amount is: 0.0 ;m2:C(C)OC(=O)N=C=S, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:CN(C)C=O, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(C)(C)NS(=O)(=O)C1=C(C=CC(=C1)NCC(=S)NC(=O)OCC)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.20 g (4.0 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide is dissolved in 5 ml of anhydrous DMF, and 0.60 g (4.3 mmol) of 95% strength ethoxycarbonyl isothiocyanate is added. After 3 h at room temperature the mixture is taken up in ethyl acetate and washed with 1N hydrochloric acid and water. The organic phase is dried over magnesium sulfate and the solvent is removed by distillation. The residue is taken up in a little ethyl acetate and precipitated with heptane at -25° C. The precipitate is filtered off with suction and dried to give 1.29 g (75% of theory) of colorless N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide. m.p.: 110° C. |
Here is a chemical reaction formula: Reactants are m3:NC1=CC=C(C#N)C=C1, amount is: 0.0 MOLE;m4:O1C(CO)C1, amount is: 0.0 MOLE;m2:C(#N)C1=CC=C(C=C1)N1C(OC(C1)COS(=O)(=O)C)=O, amount is: 0.0 ;m1:[O-]C1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC(CNC1=CC=C(C#N)C=C1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1 Equivalent of NaH is added to a solution of 1.7 g of Na p-methoxycarbonylmethylphenoxide (obtainable by converting p-hydroxybenzyl cyanide into the corresponding carboxylic acid, esterifying with methanol to give p-methoxycarbonylmethylphenol and subsequently converting the latter into the phenoxide) in 20 ml of dimethylformamide (DMF), and the mixture is stirred at room temperature for 30 min. After that, 3.0 g of 3-p-cyanophenyl-5-methanesulfonyloxymethyloxazolidin-2-one ("A") (obtainable by reacting p-aminobenzonitrile with 2,3-epoxypropan-1-ol to give p-(N-2,3-dihydroxypropylamino)benzonitrile, reacting the latter with diethyl carbonate in the presence of K tert-butoxide to give 3-p-cyanophenyl-5-hydroxymethyloxazolidin-2-one and subsequently esterifying the latter with methanesulfone chloride), dissolved in 10 ml of DMF, are added and the mixture is once again stirred at room temperature for 15 min. Following removal of the solvent, and the customary working-up, 3-p-cyanophenyl-5-(p-methoxycarbonylmethylphenoxymethyl)oxazolidin-2-one is obtained, M.p. 114°-115°. |
Here is a chemical reaction formula: Reactants are m1:S, amount is: 0.0 MOLE;m2_m3_m4:C(#N)C1=CC=C(C=C1)N1C(OC(C1)COC1=CC=C(C=C1)CC(=O)OC)=O, amount is: 0.0 ;m2_m3_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(N)(=N)C1=CC=C(C=C1)N1C(OC(C1)COC1=CC=C(C=C1)CC(=O)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: H2S gas is passed, at -10°, into a solution of 1.2 g of 3-p-cyanophenyl-5-(p-methoxycarbonyimethylphenoxymethyl)oxazolidin-2-one (obtainable in accordance with Example 1) in 50 ml of pyridine and 7 ml of triethylamine. The mixture is subsequently stirred at room temperature for 14 h and concentrated by evaporation; the residue is dissolved in 50 ml of acetone and treated with 9 ml of methyl iodide. After this mixture has been stirred for a further 6 h, it is filtered and the residue is washed with 5 ml of acetone and dissolved in 30 ml of methanol; 4.6 g of ammonium acetate are added to this solution, which is stirred at room temperature for 24 h. Following the customary working-up, 3-p-amidinophenyl-5-(p-methoxycarbonylmethylphenoxymethyl)oxazolidin-2-one (semihydriodide) is obtained, M.p. 151°-152°. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C[Si](C)(C)C#CC=1C=C(C=NC1)C1N(CCC1)C, amount is: 0.0 ;m1_m2_m3:C([O-])([O-])=O.[Cs+].[Cs+], 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:C(#C)C=1C=C(C=NC1)C1N(CCC1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Repeating the procedure of Example 16, but using trimethylsilylacetylene in place of phenylacetylene, 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine and the fumarate derivative thereof were obtained as follows. 5-Trimethylsilylethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine (516 mg, 2 mmol) and cesium carbonate (200 mg, 0.6 mmol) were dissolved in methanol (10 mL) and heated under reflux for 5 h. After cooling the solvents were removed in vacuo and the residue dissolved in ethyl acetate (40 mL) and washed with water (10 mL). The aqueous layer was extracted with ethyl acetate (40 mL) and the combined organic extracts washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:9, 1:4, 1,3) to afford 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine as an oil, 218 mg, 59%. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3_m5:BrC1=CC=C(C=C1)O, amount is: 0.0 ;m1_m2_m3_m5:N1C=NC=C1, amount is: 0.0 ;m1_m2_m3_m5:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=CC=C(C=C1)C[Si](C)(C(C)(C)C)O[Si](C(C)(C)C)(C)CC1=CC=C(C=C1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-Bromophenol (5.76 g, 30 mmol), imidazole (4.08 g, 60 mmol) and tert-butyldimethylsilyl chloride (5.02 g, 33 mmol) were stirred in anhydrous DMF (100 mL) at 25° C. for 18 h. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (2×75 mL). The combined extracts were washed with water (2×75 mL), brine (75 mL) and dried (MgSO4) before concentration in vacuo. The crude product was purified using "flash" silica gel column chromatography with ethyl acetate:hexane (1:4) as eluant to afford the title compound as an oil, 7.9 g, 92%. 1H NMR (CDCl3, 300 MHz): δ 7.33 (app. dt, J=9, 3, 1 Hz, 2 H), 6.73 (app. dt, J=9, 3, 1 Hz, 2 H) 0.98 (s, 9 H),0.21 (s, 6 H). |
Here is a chemical reaction formula: Reactants are m2:[F-].[Cs+], amount is: 0.0 ;m1_m3:[Si](C)(C)(C(C)(C)C)OC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C, 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:OC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The above-described pyridine derivative (750 mg, 2.04 mmol) was dissolved in methanol (40 mL) and cesium fluoride (620 mg, 4.08 mmol) was added. The stirred mixture was heated at reflux for 18 h under inert atmosphere. After cooling the solvent was removed in vacuo and the resulting oil was dissolved in ethyl acetate (50 mL). This was washed with water (20 mL), brine (20 mL), dried (MgSO4) and concentrated. The crude material was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:2 ) to 10% methanol: ethyl acetate as eluant to afford 5-(4-hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine 480 mg, 93% as a colorless foam, 1H NMR (CDCl3, 300 MHz): δ 8.66 (d, J=2 Hz, 1 H), 8.43 (d, J=2 Hz, 1 H), 7.90 (s, 1 H), 7.32 (d, J=9 Hz, 2 H), 6.81 (d, J=9 Hz, 2 H), 3.33 (t, J=8 Hz, 1 H), 3.22 (t, J=8 Hz, 1 H), 2.41 (m, 1 H), 2.28 (s, 3 H), 2.10 (m, 2 H), 1.93 (m, 2 H). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ;m1_m3_m2:FC(C(=O)O)(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:FC1=CC=C(C=C1)C=1C=C(C=NC1)C1NCCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The above-described pyridine derivative (1.25 g, 3.5 mmol) was dissolved in a mixture of dichloromethane (10 mL) and trifluoroacetic acid (10 mL) and this was stirred at 25° C. for 18 h. The solvents were removed in vacuo and the crude material dissolved in ethyl acetate (50 mL). Saturated sodium carbonate solution (30 mL) was added and the organic layer separated. The aqueous phase was extracted with two further portions of ethyl acetate (2×30 mL), the combined organic extracts washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel with ethyl acetate, then methanol:ethyl acetate (1:9) as eluant to afford 5-(4-fluorophenyl)-3-(2-piperidinyl)pyridine, 940 mg, 100%. NMR (CDCl3, 300 MHz): δ 8.69 (d, J=2 Hz, 1 H), 8.55 (d, J=2 Hz, 1 H), 7.93 (t, J=2 Hz, 1 H), 7.56 (m, 2 H), 7.16 (app. tm, J=9 Hz, 2 H), 3.18 (d, J=12 Hz, 1 H), 2.83 (td, J=12, 3 Hz, 1 H), 2.61 (bs exch., 1 H), 1.92 (m, 2 H), 1.45-1.75 (m, 6 H). |
Here is a chemical reaction formula: Reactants are m2_m4_m3:C(\C=C\C(=O)O)(=O)O, amount is: 0.0 MOLE;m2_m4_m3:FC1=CC=C(C=C1)C=1C=C(C=NC1)C1NCCCC1, amount is: 0.0 MOLE;m1:N1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m4_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(\C=C\C(=O)O)(=O)O.FC1=CC=C(C=C1)C=1C=C(C=NC1)C1NCCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The above described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether resulted in the formation of 5-(4-fluorophenyl)-3-(2-piperidinyl)pyridine fumarate (70%) as a colorless solid. |
Here is a chemical reaction formula: Reactants are m1_m5_m6_m2_m3_m4_m7:BrC=1C=C(C=NC1)C1N(CCC1)C, amount is: 0.0 ;m1_m5_m6_m2_m3_m4_m7:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m5_m6_m2_m3_m4_m7:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m5_m6_m2_m3_m4_m7:COCCOC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m6_m2_m3_m4_m7:O, amount is: 0.0 ,Catalysts are m1_m5_m6_m2_m3_m4_m7:[Pd], amount is: 0.0 ;m1_m5_m6_m2_m3_m4_m7:[Cu]I, amount is: 0.0 .Products are 0:C(#CC)C=1C=C(C=NC1)C1N(CCC1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A Parr hydrogenation vessel was charged with 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (1 g, 4.15 mmol), 10% palladium on charcoal (106 mg, 0.1 mmol), copper(I)iodide (38 mg, 0.2 mmol), triphenylphosphine (104 mg, 0.4 mmol) and potassium carbonate (1.38 g, 10 mmol), DME (10 mL) and water (10 mL). The vessel was evacuated and propyne gas was introduced to a pressure of 20 p.s.i. The mixture was agitated and heated at 90° C. for 6 days, readmitting propyne gas as necessary. Analysis by GC at this stage indicated about 40% completion and the cooled mixture was filtered through celite and the filtrate concentrated in vacuo. The mixture was then acidified with 1M HCl (50 mL) and extracted with toluene (50 mL). The aqueous layer was made basic with solid potassium carbonate and extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extracts were washed with water (50 mL), dried (MgSO4) and concentrated to afford an oil. The crude product was purified by silica gel column chromatography with ethyl acetate:hexane (1:1) as eluant to afford 5-propynyl-3-(1-methyl-2-pyrrolidinyl)pyridine (250 mg, 30%). A portion (225 mg) of this material was converted to the title compound by the addition of one equivalent of fumaric acid to a methanol (10 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether followed by recrystallization from ethyl acetate afforded 5-[1-(1-propynyl)]-3-(1-methyl-2-pyrrolidinyl)pyridine fumarate, 180 mg, 50%. M.p. 188°-189° C. (EtOAc); 1H NMR (DMSO-d6, 300 MHz): δ 8.49 (s, 1H), 8.47 (s, 1H), 7.77 (s, 1H), 6.60 (s, 2H), 3.34 (t, J=9 Hz, 1H), 3.25 (app. t, J=9 Hz, 1H), 2.41 (dd, J=9, 9 Hz, 1H), 2.22 (m, 1H), 2.16 (s, 3H), 2.08 (s, 3H), 1.85 (m, 2H), 1.69 (m, 1H). |
Here is a chemical reaction formula: Reactants are m4:CC(C)(C#C)O, amount is: 0.0 ;m1_m5_m8_m2_m3_m6_m7:BrC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C, amount is: 0.0 ;m1_m5_m8_m2_m3_m6_m7:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m5_m8_m2_m3_m6_m7:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m9_m10:O, amount is: 0.0 ;m9_m10:C(C)(=O)OCC, amount is: 0.0 ;m1_m5_m8_m2_m3_m6_m7:COCCOC, amount is: 0.0 ;m1_m5_m8_m2_m3_m6_m7:O, amount is: 0.0 ,Catalysts are m1_m5_m8_m2_m3_m6_m7:[Pd], amount is: 0.0 ;m1_m5_m8_m2_m3_m6_m7:[Cu]I, amount is: 0.0 .Products are 0:OC(CC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C)(C#C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5-bromo-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine (1 g, 3.06 mmol), 10% palladium on charcoal (80 mg, 0.077 mmol), copper(I)iodide (58 mg, 0.30 mmol), triphenylphosphine (80 mg, 0.30 mmol) and potassium carbonate (1.06 g, 7.65 mmol) in DME (5 mL) and water (5 mL) was stirred at 25° C. After 0.75 h 2-methyl-3-butyn-2-ol (0.74 mL, 7.65 mmol) was added and the reaction flask was heated at 80° C. for 18 h. Water (30 mL) and ethyl acetate (30 mL) were added to the cooled mixture and this was filtered through celite. The organic phase was separated and the aqueous layer extracted with ethyl acetate (3×20 mL) and the combined ethyl acetate extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography with ethyl acetate:hexane (1:3 to 1:1) as eluants to afford 5-(2-hydroxy-2-methyl-3-butynyl)-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine as an oil (772 mg, 76%). LRMS (EI) m/e 231 (M+ +H --CO2 and isobutylene), 230 (M+ --CO2 and isobutylene), 229 (M+ --CO2 tBu); 1H NMR (CDCl3, 300 MHz): δ 8.56 (b-s, 1H), 8.37 (b-d, J=1.5 Hz, 1H), 7.53 (m, 1H), 4.93 (b-m, 0.5H), 4.76 (b-m, 0.5H), 3.5-3.7 (b-m, 2H), 2.36 (m, 1H), 1.75-2.0 (b-m, 3H), 1.72 (b-s, 1H), 1.63 (s, 6H), 1.45 (b-s, 3H), 1.21 (b-s, 6H). |