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Here is a chemical reaction formula: Reactants are m2:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)S)O, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:CSCCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CN(C=O)C, amount is: 0.0 ;m1_m5:CCCCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)SCSC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 31 mg (0.70 mmole) of sodium hydride (as a 55% w/w dispersion in mineral oil) were washed with anhydrous hexane and then suspended in 2 ml of dimethylformamide. 100 mg (0.35 mmole) of (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol were then added at 0° C., with stirring, to the resulting suspension. After evolution of hydrogen gas had ceased, 67 mg (0.70 mmole) of methylthiomethyl chloride were added to the mixture. The resulting mixture was then stirred at the same temperature for 1 hour. At the end of this time, the reaction mixture was partitioned between ethyl acetate and an aqueous solution of sodium chloride. The organic layer was dried and concentrated by distilling off the solvent. The crude product thus obtained was purified by column chromatography through silica gel, using a 3:1 by volume mixture of ethyl acetate and hexane as the eluent, to afford 105 mg of the title compound as a solid. A pule specimen (78 mg), melting at 108°-109° C., was obtained by recrystallization of this solid from a mixture of ethyl acetate and hexane. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N=C1SC(C(N1)=O)CC=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:Cl, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=NC=C(C=C1)CC1C(NC(S1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-imino-5-[[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methyl]-4-thiazolidinone (0.76 g), 1N HCl (10 ml) and ethanol (10 ml) was heated for 20 hours while refluxing, followed by concentration under reduced pressure. The residual crystal was collected by filtration, washed with water and then recrystallized from ethanol-chloroform to yield 5-[[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methyl]-2,4-thiazolidinedione (0.45 g, 59%) as a colorless crystal. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:COC(C(CC=1C=CC(=NC1)OCCC=1N=C(SC1C)C1=CC=CC=C1)Br)=O, amount is: 0.0 ;m1_m2_m3:NC(=S)N, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC1=C(N=C(S1)C1=CC=CC=C1)CCOC1=NC=C(C=C1)CC1C(NC(S1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-bromo-3-[2-[2-(5-methyl-2-phenyl-4-thiazolyl)ethoxy]-5-pyridyl]propionic acid methyl ester (1.40 g), thiourea (0.25 g) and ethanol (20 ml) was heated for 4.5 hours while refluxing, followed by addition of 2N hydrochloric acid (20 ml) and heating for 18 more hours under refluxing conditions. The reaction mixture was added to water and extracted with dichloromethane. After the dichloromethane layer was washed with water and dried (MgSO4), the solvent was distilled off. The residual crystal was recrystallized from ethanol-chloroform to yield 5-[[2-[2-(5-methyl-2-phenyl-4-thiazolyl)ethoxy]-5-pyridyl]methyl]-2,4-thiazolidinedione (0.66 g, 51%) as a colorless crystal. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(=O)C=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:S1C(NC(C1)=O)=O, amount is: 0.0 ;m1_m2_m3_m4:N1CCCCC1, amount is: 0.0 ;m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=NC=C(C=C1)C=C1C(NC(S1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl) ethoxy]pyridine (0.6 g), 2,4-thiazolidinedione (0.235 g), piperidine (0.066 ml) and ethanol (20 ml) was heated for 9 hours while refluxing. The reaction mixture was poured into water; the separating crystal, collected by filtration, was then recrystallized from ethanol-chloroform to yield 5-[[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methylidene]-2,4-thiazolidinedione (0.232 g, 29%) as a yellow crystal. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=NC=C(C=C1)C=C1C(NC(S1)=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCCC1, amount is: 0.0 ,Catalysts are m1_m2_m3:[C].[Pd], amount is: 0.0 .Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=NC=C(C=C1)CC1C(NC(S1)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5-[[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-pyridyl]methylidene]-2,4-thiazolidinedione (1.00 g), palladium-carbon (5%, 1.00 g) and tetrahydrofuran (80 ml) was subjected to catalytic reduction at room temperature and 1 atom for 6 hours. The catalyst was filtered off, and palladium-carbon (2.00 g) was added and the mixture was further subjected to catalytic reduction at room temperature and 1 atom for 6 hours. The catalyst was filtered off. The filtrate was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography. From the fraction eluted with 2% methanol-chloroform, crystals (520 mg, 52%) of 5-[[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-pyridyl]methyl]-2,4-thiazolidinedione were obtained. Recrystallization from dichloromethane-isopropyl ether gave colorless prisms. Melting point: 151°-152° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:CC1=C(N=C(O1)C1=CC=CC=C1)CCOC1=NC=C(C=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m3_m2_m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:CO, amount is: 0.0 ,Catalysts are m1_m3_m2_m4:[C].[Pd], amount is: 0.0 .Products are 0:NC=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-nitropyridine (13.4 g), palladium-carbon (5%, 1.5 g), ethyl acetate (200 ml), and methanol (150 ml) was catalytically reduced at room temperature at 1 atm. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residual crystal was collected by filtration and recrystallized from ethyl acetate-hexane to yield 5-amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (11.4 g, 93%) as a brown crystal. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m6:COC(C(CC=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1)Br)=O, amount is: 0.0 ;m1_m2_m3_m6:NC(=S)N, amount is: 0.0 ;m1_m2_m3_m6:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m4_m5:C(=O)(O)[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m6:C(C)O, amount is: 0.0 ;m4_m5:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:N=C1SC(C(N1)=O)C=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-bromo-3-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]propionic acid methyl ester (1.07 g), thiourea (0.2 g), sodium acetate (0.22 g) and ethanol (25 ml) was heated for 2.5 hours while refluxing. To the reaction mixture was added a saturated aqueous solution of NaHCO3 and ether, and the resulting crystal was collected by filtration, to yield 2-imino-5-[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]-4-thiazolidinone (0.86 g, 88%) (recrystallized from chloroform-methanol) as a colorless crystal. |
Here is a chemical reaction formula: Reactants are m4_m6:[I-].[K+], amount is: 0.0 ;m1_m2_m7:NC=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m7:Cl, amount is: 0.0 ;m3_m5:N(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m6:O, amount is: 0.0 ;m1_m2_m7:CC(=O)C, amount is: 0.0 ;m3_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 5-amino-2-[2-(5-methyl-2-phenyl-4-oxazolyl) ethoxy]pyridine (10.0 g), conc. HCl (8.47 ml) and acetone (100 ml), a solution of sodium nitrite (NaNO2) (2.46 g) in water (10 ml) was added dropwise at a temperature of under 10° C. After mixture was stirred at 10° C. for 30 minutes, a solution of potassium iodide (KI) (2.46 g) in water (10 ml) was added dropwise to the mixture. The reaction mixture was stirred at 30° to 35° C. for 1 hour and then at 35° to 40° C. for 1 hour, after which it was concentrated under reduced pressure. The residue was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residual oily substance was subjected to silica gel chromatography. From the fraction eluted with ethyl acetate-hexane (1:3, v/v), 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (7.22 g, 52%) was obtained, which was then recrystallized from ethyl acetate-hexane to yield a colorless crystal. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m5:IC=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, amount is: 0.0 ;m1_m4_m2_m5:C(CCC)[Li], amount is: 0.0 MOLE;m3:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m5:O1CCCC1, amount is: 0.0 ;m1_m4_m2_m5:CCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)C=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl) ethoxy]pyridine (2.5 g) in tetrahydrofuran (40 ml), a solution of n-butyl lithium in hexane (1.6M, 4.61 ml) was added dropwise at -65° C. in a nitrogen stream. After the mixture was stirred at the same temperature for 15 minutes, N,N-dimethylformamide (0.71 ml) was added dropwise. After the cooling bath was removed and the mixture was stirred for 30 more minutes, a saturated aqueous solution of ammonium chloride (6 ml) was added. The reaction mixture was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure, to yield 5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (1.5 g, 79%), which was then recrystallized from ethyl acetate-hexane to yield a colorless crystal. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(=O)NC(C(C)=O)CC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:Cl, 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:Cl.NC(C(C)=O)CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3-acetylamino-4-phenyl-2-butanone (12.5 g), 6N HCl (50 ml) and ethanol (50 ml) was stirred under refluxing conditions for 18 hours. The reaction mixture was concentrated under reduced pressure to yield 3-amino-4-phenyl-2-butanone hydrochloride (9.8 g, 81%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)OC(CC(=O)NC(C(C)=O)CC1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2_m3:P(=O)(Cl)(Cl)Cl, 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(C1=CC=CC=C1)C=1N=C(OC1C)CC(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(1-benzyl-2-oxopropyl)malonamidic acid ethyl ester (7.0 g), phosphorus oxychloride (POCl3) (5.8 g) and toluene (40 ml) was stirred under refluxing conditions for 1 hour. The reaction mixture was concentrated under reduced pressure; the residue was then neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure and the residue was subjected to silica gel chromatography. From the fraction eluted with hexane-ethyl acetate (1:3, v/v), ethyl 2-(4-benzyl-5-methyl-2-oxazolyl)acetate (4.76 g, 63%) was obtained as an oily substance. |
Here is a chemical reaction formula: Reactants are m3:O, amount is: 0.0 ;m2_m5:C(C1=CC=CC=C1)C=1N=C(OC1C)CC(=O)OCC, amount is: 0.0 ;m1_m4:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C(C)OCC, amount is: 0.0 ;m1_m4:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)C=1N=C(OC1C)CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of lithium aluminum hydride (LiAlH4) (0.7 g) in ethyl ether (40 ml), a solution of ethyl 2-(4-benzyl-5-methyl-2-oxazolyl)acetate (4.76 g) in ethyl ether (60 ml) was added dropwise under ice cooling conditions, followed by stirring for 1 hour. After water (5 ml) was added dropwise to the reaction mixture, the insoluble substances were filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography. From the fraction eluted with chloroform-ethyl acetate (2:1, v/v), 2-(4-benzyl-5-methyl-2-oxazolyl)ethanol (3.0 g, 75%) was obtained as an oily substance. |
Here is a chemical reaction formula: Reactants are m1_m6_m10_m2:NC=1C=CC(=NC1)OCC=1N=C(OC1C)C1=CC=CC=C1, amount is: 0.0 ;m1_m6_m10_m2:Cl, amount is: 0.0 ;m4_m8:[I-].[Na+], amount is: 0.0 ;m3_m7:N(=O)[O-].[Na+], amount is: 0.0 MOLE;m5:C(O)([O-])=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m6_m10_m2:CC(=O)C, amount is: 0.0 ;m1_m6_m10_m2:O, amount is: 0.0 ;m9:O, amount is: 0.0 MOLE;m4_m8:O, amount is: 0.0 ;m3_m7:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:IC=1C=CC(=NC1)OCC=1N=C(OC1C)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5-amino-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (7.10 g) in acetone (200 ml)-water (50 ml) was added dropwise concentrated hydrochloric acid (7.46 g) under ice cooling, and then solution of sodium nitrite (1.83 ) in water (10 ml) was added dropwise. The mixture was stirred for 10 minutes. To the mixture was added a solution of sodium iodide (4.40 g) in water (20 ml) under ice cooling. The mixture was stirred at 15°-20° C. for 2 hours. To the reaction mixture was added water, and the mixture was neutralized with a solution of sodium hydrogen carbonate. The mixture was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel chromatography. From the fraction eluted with ethyl acetate-hexane (1:9, v/v), crystals (6.65 g, 67%) of 5-iodo-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine were obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms. Melting point: 129°-130° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:CC1=C(N=C(O1)C1=C(C=CC=C1)Cl)CCOC1=NC=C(C=C1)[N+](=O)[O-], amount is: 0.0 ;m1_m3_m2_m4:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:O, amount is: 0.0 ,Catalysts are m1_m3_m2_m4:[Fe], amount is: 0.0 .Products are 0:NC=1C=CC(=NC1)OCCC=1N=C(OC1C)C1=C(C=CC=C1)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-[2-[5-methyl-2-(2-chlorophenyl)-4-oxazolyl]ethoxy]-5-nitropyridine (1.69 g), iron dust (787 mg), acetic acid (25 ml) and water (8 ml) was stirred at 65°-70° C. for 3 hours. Insolubles were filtered off and the filtrate was evaporated under reduced pressure. To the residue was added water. The mixture was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. The solvent was distilled off, and the residue was subjected to silica gel chromatography. From the fraction eluted with methanol-chloroform (1:25, v/v), 5-amino-2-[2-[5-methyl-2-(2-chlorophenyl)-4-oxazolyl]ethoxy]pyridine (1.50 g, 97%) was obtained. |
Here is a chemical reaction formula: Reactants are m3:CI, amount is: 0.0 ;m1:[H-].[Na+], amount is: 0.0 ;m2:C(#N)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)NC=1C=CC=CC14)C(NC3)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)N(C=1C=CC=CC14)C)C(NC3)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 36 mg (1.2 mmole) sodium hydride (80% in mineral oil) are suspended under an atmosphere of nitrogen in 50 mL dry dimethylformamide and 365 mg (1 mmole) 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole added portionwise thereto at ambient temperature. After subsidence of the gas evolution, stirring is continued for 1 hour at 20° C. 0.08 mL (1.25 mmole) methyl iodide is then added thereto and stirring continued for 16 hours at ambient temperature. The solvent is distilled off in a vacuum and the residue is chromatographed on silica gel with toluene/ethanol (95:5 v/v). The fraction with an Rf of 0.3 in dichloromethane/methanol (95:5 v/v) is isolated and recrystallized from tetrahydrofuran. 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of pale yellow crystals which decompose above 270° C. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)(C)(C)OC(=O)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)NC=1C=CC=CC14)C(NC3)=O, amount is: 0.0 ;m2:O1CCOCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(O)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)NC=1C=CC=CC14)C(NC3)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 147 mg (0.33 mmole) 12-(2-tert.-butoxycarbonylethyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole are stirred for 16 hours at 20° C. in 5 mL 18% hydrochloric acid and 5 mL dioxan and then for 2 hours at 50° C. The product formed is filtered off, washed with a little water and ethanol and dried in a vacuum at 90° C. 12-(2-Carboxyethyl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of pale beige crystals which decompose above 320° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(#N)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)N(C=1C=CC=CC14)C)C(NC3)=O, amount is: 0.0 ;m1_m3_m2:C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].[Pb+4], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)N(C=1C=CC=CC14)C)C(NC3O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 140 mg (0.37 mmole) 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo[2,3a]pyrrolo[3,4-c]carbazole (Example 2) are stirred for 2 days at 20° C. in 20 mL glacial acetic acid with 197 mg (0.44 mole) lead tetraacetate. The solvent is evaporated in a vacuum and the residue partitioned between 50 mL tetrahydrofuran and 50 mL of saturated sodium hydrogencarbonate solution. The tetrahydrofuran phase is separated, washed with saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 (v/v) and dichloromethan/methanol 98:2 (v/v). The fraction with an Rf of 0.1 in toluene/ethyl acetate 3:1 (v/v) is isolated. 12-(2-Cyanoethyl)-6,7,12,13-tetrahydro-7-hydroxy-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of beige crystals which decompose above about 220° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(#N)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)N(C=1C=CC=CC14)C)C(NC3)=O, amount is: 0.0 ;m1_m2:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)CCN1C2=CC=CC=C2C=2C3=C(C4=C(C12)N(C=1C=CC=CC14)C)C(NC3OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 356 mg (0.94 mmole) 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo[2,3a]pyrrolo[3,4-c]carbazole (Example 2) are stirred for 16 hours at 20° C. in 50 mL glacial acetic acid and 1 mL methanol. The further preparation is carried out in Example 4 and the crude product is chromatographed on silica gel with dichloromethane/methanol 199:1 (v/v). The fraction with an Rf of 0.25 in toluene/ethyl acetate 4:1 (v/v) is isolated. 12-(2-Cyanoethyl)-6,7,12,13-tetrahydro-7-methoxy-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of beige crystals which decompose above about 200° C. |
Here is a chemical reaction formula: Reactants are m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ;m1_m5:C(CCCCCCCCCCC)(=O)O, amount is: 0.0 ;m3_m4_m7:[Si](C)(C)(C(C)(C)C)OC1CCNCC1, amount is: 0.0 MOLE;m3_m4_m7:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m8:C(Cl)Cl, amount is: 0.0 ;m1_m5:C(Cl)Cl, amount is: 0.0 ;m3_m4_m7:C(Cl)Cl, amount is: 0.0 ,Catalysts are m6:CN(C=O)C, amount is: 0.0 MOLE.Products are 0:O=C(CCCCCCCCCCC)N1CCC(CC1)O[Si](C)(C)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve lauric acid (0.77 g) in methylene chloride (50 mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add this solution to a mixture off 4-(O-tert-butyldimethylsilyloxy)piperidine and triethylamine (1 mL) in methylene chloride (25 mL). Heat at reflux overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with water, and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo. Dissolve the residue in hexane (100 mL) and wash twice with 10% hydrochloric acid (50 mL), once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-4-(O-tert-butyldimethylsilyloxy)piperidine. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:O=C(CCCCCCCCCCC)N1CCC(CC1)O[Si](C)(C)C(C)(C)C, amount is: 3.5 MILLIMOLE;m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 ;m1_m2_m3_m5:O1CCCC1, amount is: 0.0 ;m4:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C(CCCCCCCCCCC)N1CCC(CC1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 1-oxododecyl-4-(O-tert-butyldimethylsilyloxy)piperidine (3.5 mmol) with a solution of acetic acid (9 mL), tetrahydrofuran (6 mL) and water (6 mL). Heat at 75° C. overnight. Cool to room temperature and make basic with 10% sodium hydroxide and extract into methylene chloride. Wash with water, then with brine and dry (Na2SO4). Evaporate the solvent in vacuo and purify by flash chromatography (5% methanol/methylene chloride) to give the title compound. 587E-115 |
Here is a chemical reaction formula: Reactants are m1_m5:C(CCCCCCCCCCC)(=O)O, amount is: 0.0 ;m3_m4_m7:[Si](C)(C)(C(C)(C)C)OC1CNCCC1, amount is: 0.0 ;m3_m4_m7:C(C)N(CC)CC, amount is: 0.0 ;m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(Cl)Cl, amount is: 0.0 ;m3_m4_m7:C(Cl)Cl, amount is: 0.0 ;m8:C(Cl)Cl, amount is: 0.0 ,Catalysts are m6:CN(C=O)C, amount is: 0.0 MOLE.Products are 0:O=C(CCCCCCCCCCC)N1CC(CCC1)O[Si](C)(C)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Dissolve lauric acid (0.77 g) in methylene chloride (50mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add, by dropwise addition, to a solution of 3-(O-tert-butyldimethylsilyloxy)piperidine (0.76 g, 3.5 mmol) and triethylamine (1 mL) in methylene chloride (20 mL). Stir overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with 10% hydrochloric acid, and once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:O=C(CCCCCCCCCCC)N1CC(CCC1)O[Si](C)(C)C(C)(C)C, amount is: 3.5 MILLIMOLE;m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 ;m1_m2_m3_m5:O1CCCC1, amount is: 0.0 ;m4:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:O=C(CCCCCCCCCCC)N1CC(CCC1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Mix 1-oxododecyl-3-(O-tert-butyldimethylsilyloxy)piperidine (3.5 mmol) with a solution of acetic acid (9 mL), tetrahydrofuran (6 mL) and water (6 mL). Heat at 75° C. overnight. Cool to room temperature and make basic with cold 10% sodium hydroxide and extract into methylene chloride. Wash with water, then with brine and dry (Na2SO4). Evaporate the solvent in vacuo and purify by flash chromatography (5% methanol/methylene chloride) to give the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C=1(C(OC)=CC=CC1)OC, amount is: 0.0 ;m1_m2_m3:BrC(C(=O)Br)(C)C, amount is: 0.0 ;m1_m2_m3:[Cl-].[Al+3].[Cl-].[Cl-], amount is: 0.0 ;m4: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:COC=1C=C(C=CC1OC)C(C(C)(C)Br)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of veratrole (1,3-dimethoxybenzene) (13.8 g), 2-bromoisobutyryl bromide (23.0 g) and aluminium chloride (14.0 g) was heated for 1 hour at 70°-80° C. After cooling, ice and hydrochloric acid were added to the reaction mixture which was then extracted with ether. The extract was washed first with water and then with 1N NaOH-solution, dried and the solvent evaporated in vacuo, yielding a pale yellow oil (12.3 g). |
Here is a chemical reaction formula: Reactants are m2:Cl, amount is: 0.0 MOLE;m1_m3:C(C)OC(C1=CC(=C(C(=C1)C)OC)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:[OH-].[Na+], amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC=1C=C(C(=O)O)C=C(C1OC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3,5-dimethyl-4-methoxybenzoic acid ethyl ester (PREPARATION 2, 10.5 g) and aqueous sodium hydroxide (20%, 100 ml) is refluxed for 18 hours. The solution is cooled and acidified with hydrochloric acid (12N, pH 2). The acidified solution is extracted with chloroform (3 X). The combined extracts are dried over sodium sulfate and concentrated under reduced pressure to give a solid which is recrystallized from ether/pet ether mixture to give the title compound, mp 189°-191°. |
Here is a chemical reaction formula: Reactants are m3:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE;m1_m2_m4:CC=1C=C(CCl)C=C(C1OC)C, amount is: 0.0 ;m1_m2_m4:B(Br)(Br)Br, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC=1C=C(CCl)C=C(C1O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3,5-Dimethyl-4-methoxybenzyl chloride (I, PREPARATION 4, 1.8 g) is added to a solution of boron tribromide (1.5 m) in dichloromethane (70 ml) at 78°. The solution is allowed gradually to warm to 20°-25° overnight. The reaction is poured into an aqueous sodium bicarbonate solution, and the phases are separated. The dichloromethane phase is washed once with water and then with concentrated hydrochloric acid. The dried (sodium sulfate) organic phase is concentrated under reduced pressure to give the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m7:C(#N)[BH3-].[Na+], amount is: 0.0 ;m1_m2_m3_m7:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N)C, amount is: 0.0 ;m1_m2_m3_m7:CCC=O, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE;m5:[OH-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m7:CO, amount is: 0.0 ;m6:ClCCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1NCCC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium cyanoborohydride (0.31 g) is added to a cold solution of 1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication No. WO 88/08424, 2.8 g), propional (0.87 g), and methanol (15 ml). After the exotherm has subsided, the reaction is stirred at 20°-25° overnight. The reaction is acidified (pH 2) with aqueous hydrochloride and then diluted with dichloromethane. The pH is adjusted with aqueous ammonium hydroxide (pH 8), and the phases are separated. The organic phase is dried over sodium sulfate, and concentrated under reduced pressure to a crude product which is dissolved in diethyl ether and allowed to crystallize at -5°. The solid is identified as starting material. The mother liquor is concentrated in vacuo to give the title compound. |
Here is a chemical reaction formula: Reactants are m4:C(#N)[BH3-].[Na+], amount is: 0.0 ;m1_m8:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N)C, amount is: 0.0 ;m7:CC(=O)C, amount is: 0.0 MOLE;m6:C(#N)[BH3-].[Na+], amount is: 0.0 MOLE;m3:C(C)(=O)O, amount is: 0.0 MOLE;m2:CC(=O)C, amount is: 0.0 ;m5:C(C)(=O)O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m8:CO, amount is: 0.0 ;m9:C(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1NC(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-[1,1-Dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication 88/08424, 2.0 g) is dissolved in 35 ml of methanol and acetone (0.48 g) is added. The reaction is cooled to 0° and acetic acid (to pH 4.0) is added. The reaction is stirred 15 min at 0° and then sodium cyanoborohydride (0.50 g) is added. The reaction is allowed to warm slowly to 20°-25° and followed by TLC until completion. Additional acetic acid, sodium cyanoborohydride and acetone are sometimes necessary to force the reaction to completion. The reaction is diluted with chloroform (100 ml), washed with saturated aqueous sodium bicarbonate (50 ml), saline (75 ml), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (75 g silica gel, 4:1 hexane/ethyl acetate) affords the title compound, NMR (300 MHz, CDCl3) 7.67, 6.91, 4.15, 3.57, 3.00, 1.48 and 1.23 δ. |
Here is a chemical reaction formula: Reactants are m1_m4:N1CCNCC1, amount is: 0.0 ;m3:ClC1=C(C=CC=C1)[N+](=O)[O-], amount is: 0.0 ;m2:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(C)#N, amount is: 0.0 ;m5:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=C(C=CC=C1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Piperazine (24.46 g) is dissolved in acetonitrile (200 ml) and anhydrous potassium carbonate (10.47 g) is added. Then 2-chloronitrobenzene (10.0 g) is added dropwise. After stirring 1 hr at 20°, the reaction mixture is diluted with methylene chloride, washed with water, and saturated aqueous potassium carbonate. After drying over anhydrous sodium sulfate, the reaction mixture is concentrated under reduced pressure to give the title compound, NMR (300 MHz, CDCl3) 7.75, 7.49, 7.14, 7.04, 3.03 and 1.93 δ. |
Here is a chemical reaction formula: Reactants are m1_m2:CC(C)(OC(=O)N1CCN(CC1)C1=C(C=CC=C1)[N+](=O)[O-])C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)O, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=C(C=CC=C1)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-[1,1-Dimethylethoxycarbonyl]-4-(2-nitrophenyl)piperazine (PREPARATION 12, 7.61 g) is dissolved in ethanol (150 ml). Palladium on carbon (10%, 0.75 g) is added and the reaction is hydrogenated at 45 psi for 6 hr. The mixture is filtered thru celite and concentrated under reduced pressure to give the title compound. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(#N)[BH3-].[Na+], amount is: 0.0 ;m1_m2_m3:CC(C)(OC(=O)N1CCN(CC1)C1=C(C=CC=C1)N)C, amount is: 0.0 ;m1_m2_m3:C(C)=O, 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:CC(C)(OC(=O)N1CCN(CC1)C1=C(C=CC=C1)NCC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium cyanoborohydride (1.6 g) is added to a 0° solution of 1-[1,1-dimethylethoxycarbonyl]-4-(2-aminophenyl)piperazine (PREPARATION 13, 6.52 g) and acetaldehyde (1.48 ml) dissolved in methanol (65 ml). After 3 hr the reaction mixture is partially concentrated under reduced pressure. Then it is diluted with chloroform, washed with saturated aqueous sodium bicarbonate, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, Rf =0.62 (ethyl acetate/hexane, 1/1), NMR (300 MHz, CDCl3) 7.04, 6.95, 6.66, 4.59, 3.70-3.50, 3.15, 2.82, 1.49 and 1.28 δ. |
Here is a chemical reaction formula: Reactants are m1_m2:FC=1C=C2C=C(NC2=CC1)C(=O)O, amount is: 0.0 MOLE;m1_m2:C(C(=O)Cl)(=O)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:FC=1C=C2C=C(NC2=CC1)C(=O)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Fluorindole-2-carboxylic acid is dissolved in oxalylchloride and stirred 24 hr at 20°-25° in the dark. The reaction mixture is concentrated under reduced pressure to give the title compound. |
Here is a chemical reaction formula: Reactants are m3:C(C)(=O)O, amount is: 0.0 ;m1_m4_m2:COC1(C(=C2C=C(N=C2C(=C1)C)C(=O)OCC)C)C, amount is: 0.0 ;m1_m4_m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C(=C2C=C(NC2=C(C1C)C)C(=O)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of ethyl 5-methoxy-4,5,7 trimethylindole-2-carboxylate (PREPARATION 19, 1.04 g) in ethanol (30 ml) containing potassium hydroxide (45%, 2.5 ml) is heated under reflux for 1.5 hr. The mixture is acidified with acetic acid (2 ml) and concentrated under reduced pressure. The residue is mixed with water (200 ml) and filtered. The filter cake is washed with water and dried to give the title compound. |
Here is a chemical reaction formula: Reactants are m5:CC(C)=C, amount is: 0.0 MOLE;m2_m6:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N)C, amount is: 0.0 ;m4:B(F)(F)F.CCOCC, amount is: 0.0 ;m1:CC(C)=C, amount is: 0.0 ;m3:P(O)(O)(O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m6:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)NC=1C(=NC=CC1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Isobutylene (10 ml) is condensed into a solution of 1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication No. WO 88/08424, 200 mg) in methylene chloride (10 ml) at -70°. Phosphoric acid (85%, 50 μl) is added and the mixture stirred for 60 minutes. Boron trifluoride etherate (200 μl) is added dropwise and the resulting suspension is stirred 8 hours at reflux and overnight at 20°-25° allowing the isobutylene to evaporate. The suspension is diluted with water and ammonium hydroxide is added until basic to pH paper and then extracted with methylene chloride (3 ×). The combined extracts are dried over anhydrous potassium carbonate, filtered, and concentrated under reduced pressure to a liquid which is flash chromatographed (silica gel, 230-400 mesh), eluting with methanol/chloroform (3/20). The appropriate fractions are pooled and concentrated to give an oil. The NMR, CMR, IR, and MS (m/e) M+234 support the title compound. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3_m5:CC(C)(OC(=O)N1CCNCC1)C, amount is: 0.0 ;m1_m4_m2_m3_m5:ClC1=NC=NC(=C1[N+](=O)[O-])Cl, amount is: 0.0 ;m1_m4_m2_m3_m5:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3_m5:ClCCl, amount is: 0.0 ;m1_m4_m2_m3_m5:ClCCl, amount is: 0.0 ;m6:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=C(C(=NC=N1)Cl)[N+](=O)[O-])C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1-[1,1-dimethylethoxycarbonyl]piperazine (1.88 g) in dichloromethane (30 ml) is added drop by drop over 1.5 hr to a solution of 4,6-dichloro-5-nitropyrimidine (1.94 g) and triethylamine (1.32 g) in dichloromethane (170 ml) at - 78°. After stirring an additional hr at -78°, the reaction is diluted with aqueous sodium bicarbonate (10%). The phases are separated, the organic phase is concentrated to a liquid which solidified on standing at 20°-25°. The solid is dissolved in chloroform and flash chromatographed on silica gel eluting with methanol/chloroform (1/99), pooling and concentrating the appropriate fractions gives the title compound, Anal. Calc for C13H18N5ClO4 ; MW=343.77: C,45.42; H,5.28; N,20.37; Cl,10.31. Found: C,45.52; H,5.40; N,20.34; Cl,10.36. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=NC=CN=C1Cl, amount is: 0.0 ;m1_m2_m3:C(C)(C)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:ClC1=NC=CN=C1NC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2,3-dichloropyrazine (2.0 g) and isopropylamine (2.3 g) in toluene (8 ml) is refluxed for 40 hr. The mixture is cooled and filtered to remove isopropylamine hydrochloride. The filtrate is concentrated in vacuo to a residue which is diluted with an aqueous sodium hydroxide solution (10%) and dichloromethane. The phases are separated. The dichloromethane phase is washed with saline, dried over sodium sulfate, and concentrated to give the title compound, NMR (CDCl3) 1.28, 4.21, 5.02, 7.54 and 7.94 δ. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC1=NC=CN=C1NC(C)C, amount is: 0.0 ;m1_m2_m3:N1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C=1(C(=CC=CC1)C)C, amount is: 0.0 ;m4:Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)NC1=NC=CN=C1N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-chloro-3-(1-methylethylamino)pyrazine (PREPARATION 24, 1.6 g) and piperazine (4.3 g) in xylene (10 ml) is refluxed for 26 hr. The mixture is cooled to 0° and diluted with concentrated hydrochloric acid (8 ml). The xylene is decanted and ether is added and also decanted from the salts. The salts are diluted with excess aqueous sodium hydroxide (5%) and dichloromethane. The phases are separated. The aqueous phase is extracted three more times with dichloromethane. The combined organic extracts are dried over sodium sulfate and concentrated to give a liquid mixture which is flash chromatographed on silica gel eluting with methanol/chloroform (5/95). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.27, 1.83, 3.04, 4.12, 4.78, 7.49 and 7.72 δ. |
Here is a chemical reaction formula: Reactants are m2:N1CCNCC1, amount is: 0.0 MOLE;m1:ClC1=NC=CN=C1NC(C)(C)C, 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:CC(C)(C)NC=1C(=NC=CN1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 25 and making non-critical variations but starting with 2-chloro-3-(1,1-dimethylethylamino)pyrazine (PREPARATION 26, 0.95 g) and piperazine, the title compound is obtained, NMR (CDCl3) 1.47, 1.70, 2.99, 5.02, 7.46 and 7.69 δ. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m5:CC(C)(OC(=O)N1CCN(CC1)C1=C(C(=NC=N1)Cl)[N+](=O)[O-])C, amount is: 0.0 ;m1_m2_m4_m5:C(C)N(CC)CC, amount is: 0.0 ;m3:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4_m5:C(C)O, amount is: 0.0 ,Catalysts are m1_m2_m4_m5:[Pd], amount is: 0.0 .Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=C(C=NC=N1)N)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[4-chloro-5-nitro-6-pyrimidyl]piperazine (PREPARATION 23, 0.56 g) and triethylamine (0.3 ml) and palladium on carbon (5%, 0.13 g) in ethanol (100 ml) is charged with hydrogen gas (30 psi). After the theoretical amount of hydrogen gas is consumed, the catalyst is removed under reduced pressure. The filtrate is concentrated under reduced pressure to a foam which is diluted with an aqueous saturated solution of potassium carbonate and dichloromethane. The phases are separated and the organic phase is dried over sodium sulfate and concentrated to give to give the title compound, NMR (CDCl3) 1.49, 3.49, 3.29, 3.56, 7.98, and 8.39 δ. |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m3_m4_m6:C(#N)[BH3-].[Na+], amount is: 0.0 ;m1_m5_m2_m3_m4_m6:CC(C)(OC(=O)N1CCN(CC1)C1=C(C=NC=N1)N)C, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:CC(=O)C, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7_m8:[OH-].[Na+], amount is: 0.0 MOLE;m7_m8:ClCCl, amount is: 0.0 MOLE;m1_m5_m2_m3_m4_m6:CO, amount is: 0.0 ;m1_m5_m2_m3_m4_m6:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=C(C=NC=N1)NC(C)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of sodium cyanoborohydride (0.13 g) in methanol (4 ml) is added to a mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[5-amino-6-pyrimidinyl]piperazine (PREPARATION 28, 0.44 g), acetone (3 ml), and glacial acetic acid (0.4 ml) in methanol (7 ml) at 0°. The mixture is stirred at 20°-25° for 72 h. The reaction is diluted with an aqueous sodium hydroxide solution (10%) and dichloromethane. The phases are separated and the organic phase is washed with water and the concentrated to a colorless liquid which is flash chromatographed on silica gel eluting with methanol/chloroform (1/99). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.26, 1.49, 3.2, 3.44, 3.5-3.62, 7.89 and 8.33 δ. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:FC(C(=O)O)(F)F, amount is: 0.0 ;m1_m2_m3:CC(C)(OC(=O)N1CCN(CC1)C1=NC=NC=C1NC(C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:[OH-].[Na+], amount is: 0.0 MOLE;m1_m2_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)NC=1C(=NC=NC1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Trifluoroacetic acid (5 ml) is added to a solution of 1-[1,1-dimethylethoxy-carbonyl]-4-[5-(1-methylethylamino)-4-pyrimidinyl]piperazine (PREPARATION 29, 0.37 g) in dichloromethane (20 ml) at - 78°. The reaction is allowed to warm to 20°-25° overnight, and then diluted with excess aqueous sodium hydroxide solution (10%). The phases are separated. The aqueous phase is extracted twice again with dichloromethane. The combined organic extracts are washed with saline, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound, NMR (CDCl3) 1.25, 1.7, 3.01, 3.21, 3.45, 3.5, 7.86 and 8.34 δ. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 ;m1_m2_m4:ClC=1N=NC=C(C1NC(C)C)Cl, amount is: 0.0 ;m1_m2_m4:N1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C=1(C(=CC=CC1)C)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C(=C(N=NC1)N1CCNCC1)NC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3,5-dichloro-4-(1-methylethyl)aminopyridazine (PREPARATION 31, 1.77 g) and piperazine (2.96 g) in xylene (18 ml) is refluxed for 40 hr. The mixture is cooled and then treated with concentrated hydrochloric acid (8 ml). After further cooling, a precipitate forms and the organic liquid is separated. The aqueous phase is diluted with an excess of a solution of aqueous sodium hydroxide (10%) and then is extracted with chloroform (3 ×). The combined organic extracts are washed with water, then saline, dried over sodium sulfate, and concentrated to an oil. The crude produce is flash chromatographed on silica gel eluting with methanol. The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.20, 3.04, 3.18, 4.46, 4.73 and 8.50 δ; CMR (CDCl3) 24.0, 44.3, 45.9, 50.2, 118.2, 135.8, 148.3 and 155.4 δ. |
Here is a chemical reaction formula: Reactants are m1:ClC=1C(=C(N=NC1)N1CCNCC1)NC(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)NC1=C(N=NC=C1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 28 and making non-critical variations but starting with 1-[5-chloro-4-(1-methylethyl)amino-3-pyridazinyl]piperazine (PREPARATION 32, 1.7 g) and triethylamine (0.81 g), the title compound is obtained, NMR (CDCl3) 1.28, 2.06, 3.05, 3.11, 3.59, 4.75, 6.39, and 8.49 δ; CMR (CDCl3) 22.2, 43.2, 46.2, 50.6, 103.7, 138.7, 148.4 and 154.5 δ. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:CNCCNC, amount is: 0.0 ;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m3_m5:ClC1=NC=CC=C1[N+](=O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)#N, amount is: 0.0 ;m3_m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(CCNC)C1=NC=CC=C1[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of N,N'-dimethylethylenediamine (3.2 ml) and potassium carbonate (830 mg) in acetonitrile (15 ml) stirred at 20°-25° under a nitrogen atmosphere is added a solution of 2-chloro-3-nitropyridine (500 mg) in acetonitrile (10 ml) over one hour. The mixture is concentrated under reduced pressure and partitioned between methylene chloride (75 ml) and water (25 ml). The phases are separated and the aqueous phase is extracted with methylene chloride (25 ml) and the total organics are dried with saline and sodium sulfate. Concentration under reduced pressure gives the title compound, NMR (CDCl3) 8.29, 8.10, 6.69, 3.85, 2.90, 2.88 and 2.46 δ. |
Here is a chemical reaction formula: Reactants are m4:CNCCO, amount is: 0.0 ;m1_m2_m3_m5:CNCCO, amount is: 0.0 ;m1_m2_m3_m5:ClC1=NC=CC=C1[N+](=O)[O-], amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(C1=NC=CC=C1[N+](=O)[O-])CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(Methylamino)ethanol (3.04 ml) is added to a mixture of 2-chloro-3-nitropyridine (3.00 g) and of potassium carbonate (5.22 g) in acetonitrile (90 ml) at 0°. The mixture is stirred for 2.5 hr at 20°-25° and additional 2-(methylamino)ethanol (1.5 ml) is added. The mixture is stirred for 1.5 hr, concentrated to a gum and diluted with methylene chloride (85 ml) and water (20 ml). The layers are separated and the organic phase is washed in water and dried over magnesium sulfate. Removal of solvent under reduced pressure gives the title compound, NMR (CDCl3) 8.27, 8.14, 6.76, 4.38, 3.88 and 2.87 δ. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ;m1_m2_m4:N1C(=CC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m3:CNCCO, 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:CN(C(=O)C=1NC2=CC=CC=C2C1)CCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1,1'-carbonyldiimidazole (1.11 g) is added to a solution of indole-2-carboxylic acid (1.0 g) in tetrahydrofuran (15 ml). The mixture is stirred 1 hour at 20°-25° and 2-(methylamino)ethanol (5.0 ml) is added. The mixture is stirred 21 hours at 20°-25° and 24 hours at reflux. The mixture is concentrated under reduced pressure, diluted with methylene chloride and extracted with water and saturated sodium bicarbonate. The phases are separated and the organic phase is dried with saline and sodium sulfate and concentrated to give the crude product. Chromatography on silica gel with a methanol/chloroform gradient followed by recrystallization from chloroform/ether to give the title compound, mp 141°-142.5°. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N)C, amount is: 0.0 ;m1_m2_m3_m5:BrCCCCBr, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4:BrC(C)C(C)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)#N, amount is: 0.0 ;m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N1CCCC1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-[1,1-Dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication No. WO 88/08424, 0.50 g), 1,4-dibromobutane (0.21 ml) and potassium carbonate (0.30 g) are refluxed in 4 ml of acetonitrile for 1 week. After 1 week, additional dibromobutane (0.21 ml) is added and refluxing is continued for 3 days. The reaction mixture is poured into water, extracted with methylene chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate is purified by flash chromatography eluting with ethyl acetate/hexane (10/90) to ethyl acetate/hexane (25/75). The appropriate fractions are pooled and concentrated to give the title compound, NMR (300 MHz, CDCl3) 7.78, 6.98, 6.78, 3.52, 3.20-3.10, 1.87 and 1.44 δ. |
Here is a chemical reaction formula: Reactants are m1_m4:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N1CCCC1)C, amount is: 0.0 ;m3:[OH-].[Na+], amount is: 0.0 MOLE;m2:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCCC1)C=1C(=NC=CC1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-pyrrolidinyl)-2-pyridinyl]piperazine (PREPARATION 47, 0.26 g) is dissolved in 1.3 ml of THF and cooled to 0°. Trifluoroacetic acid (1.3 ml) is added and the reaction is stirred at 0° for 20 min, and then warmed to 20°-25° for 20 min. Then the reaction is poured into 1N aqueous sodium hydroxide and extracted with methanol/chloroform (10/90, 2×50 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, NMR (300 MHz, CDCl3) 7.64, 6.81, 6.61, 3.05-2.94, 2.86-2.79 and 1.78-1.65 δ. |
Here is a chemical reaction formula: Reactants are m2:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m3_m5:ClC1=NC=CC=C1[N+](=O)[O-], amount is: 0.0 ;m1_m4:N1CCNCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C(C)#N, amount is: 0.0 ;m1_m4:C(C)#N, amount is: 0.0 ;m6:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C(=NC=CC1)N1C=CN=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Homopiperazine (15.58 g) is dissolved in 100 ml of acetonitrile. Potassium carbonate (8.7 g) is added and then the 2-chloro-3-nitropyridine (5.0 g) dissolved in 25 ml of acetonitrile is added dropwise. The reaction is stirred at 20°-25° 4 hr, then diluted with methylene chloride, washed with water (2 ×), saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, NMR (300 MHz, CDCl3) 8.30, 8.08, 6.66, 3.60, 3.41, 3.10, 2.89 and 1.93 δ. |
Here is a chemical reaction formula: Reactants are m3:C(C1=CC=CC=C1)OC(=O)Cl, amount is: 0.0 ;m1_m4:NC=1C=C2C=C(NC2=CC1)C(=O)OCC, amount is: 0.0 ;m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(Cl)Cl, amount is: 0.0 ;m5:C(Cl)(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC=1C=C2C=C(NC2=CC1)C(=O)OCC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl 5-aminoindole-2-carboxylate [J. Am. Chem. Soc. 80, 4621 (1958) JCS Perkin I 53 (1977), 0.50 g] is dissolved in 49 ml of methylene chloride and pyridine (0.20 g) is added. The reaction is cooled to 0° and benzylchloroformate (0.36 ml) is added dropwise over 10 min. The reaction is stirred for 1 hr, diluted with chloroform, washed with saturated aqueous sodium bicarbonate, water, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate is purified by flash column chromatography (150 g silica gel) eluting with hexane/ethyl acetate (3/1). The appropriate fractions are pooled and concentrated to give the title compound, NMR (300 MHz, CDCl3) 8.90, 7.79, 7.41-7.33, 7.24, 7.16, 5.22, 4.40 and 1.41 δ. |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 ;m1:C(C1=CC=CC=C1)OC(=O)NC=1C=C2C=C(NC2=CC1)C(=O)OCC, amount is: 0.0 MOLE;m2:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ;m4:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)NC=1C=C2C=C(NC2=CC1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethyl 5-Benzyloxycarbonylaminoindole-2-carboxylate, (PREPARATION 56, 0.76 g) is dissolved in 1,4-dioxane (5.6 ml) and water (0.56 ml). Crushed potassium hydroxide (0.23 g) is added and the reaction is heated to 50° for 5 hr. The reaction is neutralized by adding 4.05 ml of 1N aqueous hydrochloric acid. The reaction is extracted with THF/chloroform (10/90, 3 ×), saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title acid, NMR (300 MHz, d4-CD3OD) 7.64, 7.34-7.15, 6.98 and 5.09 δ. |
Here is a chemical reaction formula: Reactants are m2_m1:COC1=CC=C(C=C(C(=O)OC)N=[N+]=[N-])C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m1:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=CC=C2C=C(NC2=C1)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Toluene (185 ml) is added to methyl 4-methoxy-α-azidocinnamate (PREPARATION 61, 7.73 g) and the reaction is brought to reflux and maintained at reflux for 3 hr. Then the reaction is concentrated under reduced pressure and triturated with hexane. The solids are filtered and dried under reduced pressure to give the title indole, HRMS Calcd. for C11H11NO3 : 205.0739, found: 205.0736; NMR (300 MHz, CDCl3) 8.75, 7.47, 7.11, 6.76-6.73, 3.86, and 3.79 δ. |
Here is a chemical reaction formula: Reactants are m2_m3:O, amount is: 0.0 ;m2_m3:[OH-].[K+], amount is: 0.0 ;m1_m4:COC1=CC=C2C=C(NC2=C1)C(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1=CC=C2C=C(NC2=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 6-methoxyindole-2-carboxylate (PREPARATION 62, 5.71 g) is dissolved in 70 ml of dioxane and 7 ml of water and 1.87 g of crushed potassium hydroxide are added. The reaction is heated to 50° and stirred 1.5 hr. The reaction mixture is acidified to pH 4-5 and extracted several times with methanol/chloroform (10/90). The organic layers are combined and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title acid, NMR (300 MHz, d4-CD3OD) 7.47, 7.08, 6.90, 6.72 and 3.82 δ. |
Here is a chemical reaction formula: Reactants are m2:CC(CC)=O, amount is: 0.0 ;m1:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N)C, amount is: 0.0 ;m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1NC(CC)C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 8 and making non-critical variations but starting with 1-[1,1-dimethylethoxycarbonyl]-4-[(3-amino)-2-pyridinyl)piperazine (International Publication No. WO 88/08424, 1.0 g), 2-butanone (0.27 g) sodium cyanoborohydride (0.23 g), acetic acid (5.1 ml) and methanol, the title compound is obtained, NMR (300 MHz, CDCl3) 7.68, 6.94, 6.86, 4.18, 3.56, 3.33, 3.05, 1.53, 1.47, 1.18 and 0.96 δ. |
Here is a chemical reaction formula: Reactants are m1:C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C1=NC=CC=C1N, amount is: 0.0 ;m2:CCC(CC)=O, amount is: 0.0 ;m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C1=NC=CC=C1NC(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 8 and making non-critical variations but starting with 1-[benzyloxycarbonyl]-4-[(3-amino)-2-pyridinyl]piperazine (PREPARATION 100 10.5 g), 3-pentanone (0.15 g) sodium cyanoborohydride (0.11 g), acetic acid (52.3 ml) and methanol (3.2), the title compound is obtained, NMR (300 MHz, CDCl3) 7.66, 7.38-7.33, 6.90, 6.79, 5.17, 4.21, 3.65, 3.15, 3.04, 1.66-1.46 and 0.93 δ. |
Here is a chemical reaction formula: Reactants are m1:C1OC=2C=C3C=C(NC3=CC2O1)C(=O)OC, amount is: 0.0 ;m2:[OH-].[K+], 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:C1OC=2C=C3C=C(NC3=CC2O1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 63 and making non-critical variations but starting with methyl 5,6-methylenedioxyindole-2-carboxylate (PREPARATION 78, 4.77 g), potassium hydroxide (1.47 g), the title compound is obtained, C,H,N analysis calcd. for C10H7NO4C, 58.54; H, 3.44; N, 6.83; found: C, 58.27; H, 3.18; N, 6.95. |
Here is a chemical reaction formula: Reactants are m2:N(=[N+]=[N-])CC(=O)OC, amount is: 0.0 ;m1:BrC=1C=C(C=O)C=CC1OC, 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:BrC=1C=C(C=C(C(=O)OC)N=[N+]=[N-])C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 61 and making non-critical variations but starting with 3-bromo-4-methoxybenzaldehyde (5.0 g) and methyl azidoacetate (10.7 g), the title compound is obtained, NMR (300 MHz, CDCl3) 8.10, 7.73, 6.89, 6.79, 3.94 and 3.90 δ. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1:BrC=1C=C2C=C(NC2=CC1OC)C(=O)OC, 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:BrC=1C=C2C=C(NC2=CC1OC)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 63 and making non-critical variations but starting with methyl 5-bromo-6-methoxyindole carboxylate (PREPARATION 81, 3.31 g) and potassium hydroxide (0.98 g), the title compound is obtained, NMR (300 MHz, CD3OD) 7.79, 7.03, 7.01 and 3.89 δ. |
Here is a chemical reaction formula: Reactants are m1:BrC=1C(=CC=C2C=C(NC12)C(=O)OC)OC, amount is: 0.0 ;m2:[OH-].[K+], 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:BrC=1C(=CC=C2C=C(NC12)C(=O)O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 63 and making non-critical variations but starting with methyl 7-bromo-6-methoxyindole carboxylate (PREPARATION 81, 0.36 g) and potassium hydroxide (0.11 g), the title compound is obtained, NMR (300 MHz, CD3OD), 7.58, 7.20, 6.96 and 3.93 δ. |
Here is a chemical reaction formula: Reactants are m1:C=1(C(=CC=CC1)C=O)C, amount is: 0.0 ;m2:N(=[N+]=[N-])CC(=O)OC, 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:CC1=C(C=C(C(=O)OC)N=[N+]=[N-])C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 61 and making non-critical variations but starting with o-tolualdehyde (5.0 g), methyl azidoacetate (19.2 g), the title compound is obtained, NMR (300 MHz, CDCl3) 7.96, 7.26-7.18, 7.13, 3.92 and 2.36 δ. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1:CC1=C2C=C(NC2=CC=C1)C(=O)OC, 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:CC1=C2C=C(NC2=CC=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 63 and making non-critical variations but starting with methyl 4-methylindole-2-carboxylate (PREPARATION 85, 4.94 g), potassium hydroxide (1.75 g), the title compound is obtained, NMR (300 MHz, CD3OD) 7.24, 7.19, 7.12, 6.85 and 2.51 δ. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[K+], amount is: 0.0 ;m1:CN(C)C1=CC=C2C=C(NC2=C1)C(=O)OC, 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:CN(C)C1=CC=C2C=C(NC2=C1)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 63 and making non-critical variations but starting with methyl 6-(N,N-dimethylamino)indole-2-carboxylate (PREPARATION 88, 0.80 g), potassium hydroxide (0.25 g), the title compound is obtained, NMR (300 MHz, CD3OD) 7.62, 7.13, 7.11, 7.01, and 3.11 δ. |
Here is a chemical reaction formula: Reactants are m1:[N+](=O)([O-])C1=CC=C(C=O)C=C1, amount is: 0.0 ;m2:N(=[N+]=[N-])CC(=O)OC, 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:COC(C(=CC1=CC=C(C=C1)[N+](=O)[O-])N=[N+]=[N-])=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 61 and making non-critical variations but starting with p-nitrobenzaldehyde (10 g) and methyl azidoacetate (30.4 g), the title compound is obtained, NMR 8.34, 8.07, 7.02, and 4.07 δ. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C1=NC=CC=C1[N+](=O)[O-], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2:O1CCOCC1, amount is: 0.0 ;m3:[OH-].[Na+], amount is: 0.0 ,Catalysts are m4:[Cl-].[Cl-].[Cl-].[Ti+3], amount is: 0.0 .Products are 0:C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C1=NC=CC=C1N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-[Benzyloxycarbonyl]-4-[3-nitro-2-pyridinyl]piperazine (PREPARATION 99), is dissolved in dioxane (923ml) and cooled to 0°. Then aqueous titanium trichloride (20%, 555.3 ml) is added cautiously. After stirring 30 min the reaction is diluted with aqueous sodium hydroxide solution (2N, 1.5 l) and filtered through celite. The filter cake is washed with methanol/chloroform (10/90). The combined organic layers are washed with water, saline, dried and concentrated in vacuo to afford the desired product, NMR (300 MHz, CDCl3) 7.80, 7.38-7.32, 6.99, 6.88, 5.17, 3.67 and 3.12 δ. |
Here is a chemical reaction formula: Reactants are m1_m2:C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C1=NC=CC=C1NC(C(F)(F)F)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2:C(C)O, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:FC(C(=O)NC=1C(=NC=CC1)N1CCNCC1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-[Benzyloxycarbonyl]-4-[3-(2,2,2-trifluoroacetamido)-2-pyridinyl]piperazine (PREPARATION 101), is dissolved in 70 ml of ethanol and 0.25 g of 10% palladium on carbon is added. The reaction is hydrogenated at 40 psi for 20 hr. Then it is filtered through a pad of celite and concentrated in vacuo to afford the title compound which is used without further purification, NMR (300 MHz, CDCl3) 8.51, 8.21, 7.19, and 3.45-3.47 δ. |
Here is a chemical reaction formula: Reactants are m1_m3:FC(C(=O)NC=1C(=NC=CC1)N1CCNCC1)(F)F, amount is: 0.0 MOLE;m2:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(CNC=1C(=NC=CC1)N1CCNCC1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1-[3-(2,2,2-Trifluoroacetamido)-2-pyridinyl]piperazine (PREPARATION 102), is dissolved in 5 ml of tetrahydrofuran and cooled to 0°. Then 4.84 ml of lithium aluminum hydride solution is added dropwise. After 10 min of stirring at 0°, the reaction is warmed to 20°-25° and stirred 45 min. The reaction is quenched at 0° with the dropwise addition of 0.4 ml of water, 0.6 ml of 10% aqueous sodium hydroxide, and 1 ml of water. The slurry is filtered through celite, washed with 20% methanol/chloroform and concentrated in vacuo to afford the title amine which is used without further purification, NMR (300 MHz, CDCl3), 7.82, 6.97-6.92, 4.86, 3.75, and 3.06-3.01 δ. |
Here is a chemical reaction formula: Reactants are m1:FCC(=O)Cl, amount is: 0.0 ;m2:C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C1=NC=CC=C1N, 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)OC(=O)N1CCN(CC1)C1=NC=CC=C1NC(CF)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 101 and making non-critical variations but starting with fluoroacetyl chloride (0.94 g), 1-benzyloxycarbonyl-4-[3-amino-2-pyridinyl]piperazine (PREPARATION 100, 3.0 g), the title compound is obtained, NMR (300 MHz, CDCl3) 8.83, 8.65, 8.14, 7.38-7.32, 7.12, 5.17, 4.96, 3.70 and 3.07 δ. |
Here is a chemical reaction formula: Reactants are m2:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ;m1:FCC(=O)NC=1C(=NC=CC1)N1CCNCC1, 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:FCCNC=1C(=NC=CC1)N1CCNCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 103 and making non-critical variations but starting with 1-[3-(2-fluoroacetamido)-2-pyridinyl]piperazine (PREPARATION 105, 1.4 g), lithium aluminum hydride (11.76 ml, 1M in tetrahydrofuran), the title compound is obtained. |
Here is a chemical reaction formula: Reactants are m1:N1CCNCCC1, amount is: 0.0 ;m2:ClC1=NC=CN=C1NC(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC(C)NC=1C(=NC=CN1)N1C=CN=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 24 and making non-critical variations but starting with homopiperazine (2.46 g) and 2-chloro-3-(1-methylethyl)aminopyrazine (PREPARATION 23), the title compound is obtained, NMR (300 MHz, CDCl3) 7.56, 7.34, 4.75, 4.04, 3.28-3.18, 3.00-2.94, 1.79, and 1.15 δ. |
Here is a chemical reaction formula: Reactants are m1:C(C)(C)(C)N, amount is: 0.0 ;m2:ClC=1N=NC=C(C1Cl)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:ClC=1N=NC=C(C1NC(C)(C)C)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of PREPARATION 31 and making non-critical variations but starting with t-butylamine (66.5 ml), and 3,4,5-trichloropyridazine, the title compound is obtained, NMR (300 MHz, CDCl3) 8.50, 5.09, and 1.55 δ. |
Here is a chemical reaction formula: Reactants are m1_m2_m6_m3:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1N)C, amount is: 0.0 ;m1_m2_m6_m3:BrC(=C)C, amount is: 0.0 ;m1_m2_m6_m3:C(C)#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5:ClCCl, amount is: 0.0 MOLE;m4_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE;m1_m2_m6_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCN(CC1)C1=NC=CC=C1NCC=C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[3-amino-2-pyridinyl]piperazine (International Publication 88/08424, 2.78 g), 2-bromopropene (1.87 g), anhydrous potassium carbonate (3.3 g) and acetonitrile (100 ml) is refluxed for 36 hr. The mixture is cooled and then diluted with dichloromethane and aqueous potassium carbonate solution. The phases are separated and the organic phase is washed with saline and than concentrated in vacuo. Purification by flash column chromatography (2% methanol/chloroform) provided of the title compound. Capillary GC analysis (HP1 column, initial temperature at 100° for 1 min, then programmed to rise 20° per minute to 250°) gave a peak at 6.06 (96%) minutes. |
Here is a chemical reaction formula: Reactants are m2_m3:[OH-].[K+], amount is: 0.0 MOLE;m2_m3:CC(C)(OC(=O)N1CCC(CC1)=O)C, amount is: 0.0 MOLE;m1_m7:Cl.CN, amount is: 0.0 ;m4_m8:C(#N)[BH3-].[Na+], amount is: 0.0 ;m6:Cl, amount is: 0.0 MOLE;m5:[OH-].[K+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m7:CO, amount is: 0.0 ;m4_m8:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(OC(=O)N1CCC(CC1)NC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methylamine hydrochloride (2.36 g) is dissolved in methanol (50 ml) and potassium hydroxide pellets (0.60 g) and N-(1,1-di-methylethoxycarbonyl)-4-piperidone are added. Sodium cyanoborohydride (0.69 g) in methanol (5 ml) is added and the mixture is stirred 2 hrs. Potassium hydroxide pellets (1.96 g) are added to the mixture which is stirred 1 hr and acidified to pH 2 with 6M hydrochloric acid and concentrated. The mixture is diluted with water (50 ml) and extracted with ether (3×80 ml) which is discarded. The aqueous layer is basified to pH 11 with potassium hydroxide pellets, saturated with sodium chloride and extracted with ether (6×80 ml). The combined organic extracts are dried with magnesium sulfate and concentrated to afford an oil which is chromatographed on silica gel with a methanol/chloroform gradient (5-30%). Fractions are pooled on the basis of TLC (Rf =0.13, 20% methanol/chloroform) to give the title compound, NMR (CDCl3) 4.04, 2.79, 2.54, 2.46, 2.33, 1.88, 1.46, and 1.26 δ. |
Here is a chemical reaction formula: Reactants are m1:CC=1C=C(CCl)C=C(C1OC)C, amount is: 0.0 ;m2:C(CC)NC=1C(=NC=CC1)N1CCNCC1, 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=C(CN2CCN(CC2)C2=NC=CC=C2NCCC)C=C1C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 1 and making non-critical variations but starting with 3,5-dimethyl-4-methoxybenzyl chloride (I, PREPARATION 4, 0.41 g) and 1-[3-(propylamino)-2-pyridinyl]piperazine (II, PREPARATION 7, 0.42 g), the title compound is obtained. |
Here is a chemical reaction formula: Reactants are m4:C([O-])(O)=O.[Na+], amount is: 0.0 ;m1_m2_m5:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ;m1_m2_m5:COC=1C=C2C=C(NC2=CC1)C(=O)O, amount is: 0.0 MOLE;m3_m6:C(CC)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:CCOCC, amount is: 0.0 ;m1_m2_m5:O1CCCC1, amount is: 0.0 ;m3_m6:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CCOC1=CC=CC=C1N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1,1'-Carbonyldiimidazole (1.30 g) is added to a 20°-25° solution of 5-methoxyindole-2-carboxylic acid (I, 1.39) in tetrahydrofuran (14 ml). The reaction is stirred one hour, then cooled to 0° and 1-(2-ethoxyphenyl)piperazine (II, 1.50 g) dissolved in tetrahydrofuran (7 ml) is added via cannula. The reaction is warmed to 20°-25° and stirred 48 hours. The reaction is diluted with ether (100 ml), poured into saturated aqueous sodium bicarbonate (100 ml). The organic layers are separated and washed with saline (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from toluene to give the title compound, mp 105°-107°. |
Here is a chemical reaction formula: Reactants are m3:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ;m1:C(C1=CC=CC=C1)OC=1C=C2C=C(NC2=CC1)C(=O)O, amount is: 0.0 ;m2:C(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CCNC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)OCC5=CC=CC=C5, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16 and making non-critical variations but starting with 5-benzyloxyindole-2-carboxylic acid (1.0 g), 1-(3-ethylamino-2-pyridinyl)piperazine (International Publication WO 87/01706, 0.81 g), 1,1'-carbonyldiimidazole (0.61 g) and THF (7 ml), the title compound is obtained, mp 192°-193°. |
Here is a chemical reaction formula: Reactants are m2:CC(C)(C)NC1C(NCCN1)C1=NC=CN=C1, amount is: 2.5 MILLIMOLE;m1:FC=1C=C2C=C(NC2=CC1)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC(C)(C)NC1=NC=CN=C1N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16 and making non-critical variations but starting with 5-fluoroindole-2-carboxylic acid (0.44 g) and 3-(1,1-dimethylethylamino)-2-pyrazinylpiperazine (2.50 mmol), a solid is obtained which is recrystallized from ethyl acetate to give the title compound. |
Here is a chemical reaction formula: Reactants are m6:C(C)O, amount is: 0.0 ;m4:Cl, amount is: 0.0 MOLE;m5:[OH-].[Na+], amount is: 0.0 MOLE;m8_m1_m7:N1C(=CC2=CC=CC=C12)C(=O)OCCN(C1=NC=CC=C1[N+](=O)[O-])C, amount is: 0.0 ;m10_m2:C(#N)[BH3-].[Na+], amount is: 0.0 ;m3:C(#N)[BH3-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m9:C(C)(=O)O, amount is: 0.0 MOLE;m8_m1_m7:CO, amount is: 0.0 ;m10_m2:CC(=O)C, amount is: 0.0 ,Catalysts are m8_m1_m7:[Pd], amount is: 0.0 .Products are 0:CN(C1=NC=CC=C1NC(C)C)CCOC(=O)C=1NC2=CC=CC=C2C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Palladium black (110 mg) is added to 2-(N-methyl-N-(3-nitro-2-pyridinyl)amino)-ethyl indol-2-carboxylate (PREPARATION 37, 195 mg) in methanol (75 ml). The mixture is stirred under a hydrogen atmosphere (balloon) for 30 min at 20°-25°; filtered and concentrated to give a solid. The solid is dissolved in ethanol (12 ml) and treated with acetone (0.64 ml) and sodium cyanoborohydride (27 mg). Acetic acid is added to adjust to pH 5 as measured on moistened pH test paper. The mixture is stirred for 3.8 days during which time additional sodium cyanoborohydride (39 mg) is added in portions, adjusting the pH on each addition. The mixture is adjusted to pH 3 with aqueous hydrochloric acid (10%), neutralized with aqueous sodium hydroxide (5% ) and concentrated under reduced pressure to 5 ml. The residue is diluted with chloroform, washed with water, saturated aqueous potassium carbonate, saline and dried over magnesium sulfate. Removal of solvent under reduced pressure gives an oil which is chromatographed on silica gel (10 g, 230-400 mesh) eluting with a gradient of 10-50% ethyl acetate/hexane. The appropriate fractions are pooled and concentrated to give the title compound, mp 130°-131°. |
Here is a chemical reaction formula: Reactants are m3_m5:CNC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m1_m2_m4:FC=1C=C2C=C(NC2=CC1)C(=O)O, amount is: 0.0 ;m1_m2_m4:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:C(C)(=O)OCC, amount is: 0.0 MOLE;m3_m5:C1CCOC1, amount is: 0.0 ;m1_m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CNC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5-Fluoroindole-2-carboxylic acid (98 mg) and 1,1'-carbonyldiimidazole (95 mg) are dissolved in dry THF (1 ml) and stirred for 2 hr at 20°-25°. The resulting solution is added via canula to a -10° cooled solution of 4-[3-(methylamino)-2-pyridinyl]piperazine (117 mg) in dry THF (1 ml). The reaction mixture is then allowed to reach 20°-25° overnight. The reaction mixture is then diluted with ethyl acetate, washed with saturated sodium bicarbonate and saline, dried over magnesium sulfate, and concentrated to give a solid, which is purified on a silica gel flash column eluting with hexane/ethyl acetate (1/1). The appropriate fractions are pooled and concentrated to give a solid. Recrystallization of the solid from ethyl acetate/ether gives the title compound, mp 194°-195°. |
Here is a chemical reaction formula: Reactants are m3:C(=O)(N1C=NC=C1)N1C=NC=C1, amount is: 0.0 ;m1:COC1=CC=C2C=C(NC2=C1C)C(=O)O, amount is: 0.0 ;m2:C(C)C=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CCNC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C(=C(C=C4)OC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16 and making non-critical variations but starting with 6-methoxy-7-methylindole-2-carboxylic acid (0.23 g), 1-(3-ethyl-2-pyridinyl) piperazine (0.24 g), 1,1'-carbonyldiimidazole (0.19 g) and THF (3 ml), the title compound is obtained, mp 162°-163°. |
Here is a chemical reaction formula: Reactants are m2:N1(CCCC1)C=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m1:N1C(=CC2=CC=CC=C12)C(=O)O, amount is: 0.0 ;m3:C(C)N=C=NCCCN(C)C, 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:C1CCN(C1)C2=C(N=CC=C2)N3CCN(CC3)C(=O)C4=CC5=CC=CC=C5N4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with indole-2-carboxylic acid (0.12 g), 1-[3-(1-pyrrolidinyl)-2-pyridinyl]piperazine (PREPARATION 48, 0.17 g) and 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide (0.17 g), the title compound is obtained, mp 181°-182°. |
Here is a chemical reaction formula: Reactants are m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m3:C(C)N=C=NCCCN(C)C, amount is: 0.0 ;m1:CC=1C=C(C(=O)O)C=C(C1OC)C, 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:CC=1C=C(C(=O)N2CCN(CC2)C2=NC=CC=C2NC(C)C)C=C(C1OC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with 3,5-dimethyl-4-methoxybenzoic acid (0.075 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.101 g) and 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide (0.096 g), the title compound is obtained, mp 89°-93°. |
Here is a chemical reaction formula: Reactants are m1:FC=1C=C2C=C(NC2=CC1OC)C(=O)O, amount is: 0.0 ;m3:N=C=N, amount is: 0.0 ;m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, 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:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=CC(=C(C=C4N3)OC)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with 5-fluoro-6-methoxyindole-2-carboxylic acid (PREPARATION 92, 0.30 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.32 g) and 1-(ethyl)-3-dimethylaminopropyl) carbodiimide (0.33 g), the title compound is obtained, mp 193°-194°. |
Here is a chemical reaction formula: Reactants are m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m1:FC=1C=C2C=C(NC2=CC1OC)C(=O)O, amount is: 0.0 ;m3:C(C)N=C=NCCCN(C)C, 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:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=CC(=C(C=C4N3)OC)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with 5-fluoro-6-methoxyindole-2-carboxylic acid (PREPARATION 92, 0.30 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.32 g) and 1-(ethyl)-3-(dimethylaminopropyl) carbodiimide (0.33 g), the title compound is obtained, mp 193°-194°. |
Here is a chemical reaction formula: Reactants are m1:BrC=1C=C2C=C(NC2=CC1)C(=O)O, amount is: 0.0 ;m3:C(C)N=C=NCCCN(C)C, amount is: 0.0 ;m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, 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:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with 5-bromoindole-2-carboxylic acid (0.51 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.47 g) and 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide (0.49 g), the title compound is obtained, mp 229°-230°. |
Here is a chemical reaction formula: Reactants are m1:BrC=1C=C2C=C(NC2=CC1OC)C(=O)O, amount is: 0.0 ;m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m3:C(C)N=C=NCCCN(C)C, 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:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=CC(=C(C=C4N3)OC)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with 5-bromo-6-methoxyindole-2-carboxylic acid (PREPARATION 82, 0.40 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.33 g) and 1-(ethyl)-3-(dimethylaminopropyl) carbodiimide (0.34 g), the title compound is obtained, mp 202°-204°. |
Here is a chemical reaction formula: Reactants are m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m3:C(C)N=C=NCCCN(C)C, amount is: 0.0 ;m1:CN(C)C1=CC=C2C=C(NC2=C1)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=C(C=C4)N(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with 6-(N,N-dimethylamino)indole-2-carboxylic acid (PREPARATION 89, 0.40 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.43 g) and 1-(ethyl)-3-(dimethylaminopropyl) carbodiimide (0.45 g), the title compound is obtained, mp 153°-154°. |
Here is a chemical reaction formula: Reactants are m2:N1CCNCC1, amount is: 0.0 ;m1:[N+](=O)([O-])C=1C=C2C=C(NC2=CC1)C(=O)O, amount is: 0.0 ;m3:N=C=N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with 5-nitroindole-2-carboxylic acid (0.86 g), 1-[3-(N-isopropyl)amino)-2-pyridinyl]piperazine (0.43 g), 1-(ethyl)-3-dimethylaminopropyl)carbodiimide (0.45 g) and THF (4 ml), the title compound is obtained, mp 153°-154°. |
Here is a chemical reaction formula: Reactants are m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m1:N1C(=CC2=CC=C3C(=C12)C=CC=C3)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C5=CC=CC=C5C=C4, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with benz[g]indole-2-carboxylic acid (PREPARATION 112, 0.3 g) and 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (PREPARATION 9, 0.34 g), the title compound is obtained, m.p. 190°. |
Here is a chemical reaction formula: Reactants are m2:CC(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m1:C1=C(NC=2C=CC3=C(C12)C=CC=C3)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC5=CC=CC=C54, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16A and making non-critical variations but starting with benz[e]indole-2-carboxylic acid (PREPARATION 116, 0.5 g) and 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (PREPARATION 8, 0.52 g), the title compound is obtained, m.p. 228°-231°. |
Here is a chemical reaction formula: Reactants are m2:C(C)NC=1C(=NC=CC1)N1CCNCC1, amount is: 0.0 ;m1:COC=1C=C2C=C(NC2=CC1OC)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CCNC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=CC(=C(C=C4N3)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Following the general procedure of EXAMPLE 16 and making non-critical variations but using 5,6-dimethoxyindole-2-carboxylic acid (0.50 g) and 1-[3-ethylamino-2-pyridinyl]piperazine (0.51 g), the title compound is obtained, |
Here is a chemical reaction formula: Reactants are m1_m4:BrC(C(OC1(CC=C(C=C1)C(=CC1=CC=CC=C1)C)OC(C(Br)(F)F)(F)F)(F)F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3:C(C)#N, amount is: 0.0 ;m1_m4:C(C)#N, amount is: 0.0 ,Catalysts are m2_m3:[Zn], amount is: 0.0 MOLE.Products are 0:FC(=C(F)F)OC1=CC=C(C=C1)C(=CC1=CC=C(C=C1)OC(=C(F)F)F)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The intermediate product 4,4-bis(2-bromotetrafluoroethoxy)-α-methylstilbene (106.43 g, 0.18 mole) is added to 100 ml of acetonitrile in a 250 ml dropping addition funnel attached to a 1 liter 5-necked round bottomed flask. Zinc granules (40 mesh, 25.0 g, 0.38 mole) are added to the reactor along with 100 ml of acetonitrile, and the resulting stirred suspension is deoxygenated with nitrogen for 10 minutes by introducing nitrogen gas through a gas dispersion tube. The suspension is then heated to 75° C., at which point the addition of intermediate product solution in acetonitrile is begun. The addition is carried out over 20 minutes, and the resulting mixture is heated at 75° C. overnight. After centrifugation to remove suspended solids, the resulting supernatant is evaporated to dryness, leaving a crude product which is filtered through a short bed (4 cm) of alumina in a 600 ml sintered glass filter funnel using hexane as the eluent. After removal of the hexane by evaporation, the product is heated at 55° C. under high vacuum for 30 minutes. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N1CCCCC1, amount is: 0.0 ;m1_m2_m3:[N+](#[C-])CC(=O)OCC, 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:[N+](#[C-])CC(=O)N1CCCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 48.7 g (570 mmol) of dry piperidine were added to 25.8 g (228 mmol) of ethyl isocyanoacetate in 200 ml of dry methanol, and the mixture was stirred at room temperature overnight. It was subsequently evaporated to dryness and crystallized from ether/isopropanol to give 33 g (=95% of theory) of pure N-isocyanoacetylpiperidine as beige solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(#N)C1=CC=C(C=C1)C1CN(CCC1)C(C(C)[N+]#[C-])=O, amount is: 0.0 ;m1_m2_m3_m4:O1CCOCC1, amount is: 0.0 ;m1_m2_m3_m4:Cl, amount is: 0.0 ;m1_m2_m3_m4:C(Cl)Cl.CO, 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:Cl.C(#N)C1=CC=C(C[C@H](N)C(=O)N2CCCCC2)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 17.4 g (59.2 mmol) of 3-(p-cyanophenyl)-2-isocyanopropionylpiperidine were stirred together with 160 ml of dioxane and 24 ml of concentrated hydrochloric acid at 60° C. for 45-60 min (TLC monitoring, mobile phase CH2Cl2 /CH3OH 9/1), and then the mixture was concentrated under reduced pressure, the residue was taken up in water, the aqueous phase was extracted with a little ethyl acetate, mixed with ammonia and extracted with methylene chloride, and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was taken up in acetone, and the hydrochloride was precipitated with hydrochloric acid in ether. The precipitate was filtered off with suction and washed with ether to give 16.3 g (=83%) of p-cyanophenylalaninylpiperidine hydrochloride as white solid. |
Here is a chemical reaction formula: Reactants are m1_m4:N[C@H](CCC(=O)[O-])C(=O)[O-], amount is: 0.0 MOLE;m2:[OH-].[Na+], amount is: 0.0 ;m3:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N[C@H](CCC(=O)O)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 29.5 g (80.7 mmol) of dimethyl N-(2-naphthalenesulfonyl)-L- or D-glutamate were dissolved in 500 ml of methanol and stirred with 170 ml (340 mmol) of 2N sodium hydroxide solution overnight. The pH was adjusted to 1 with concentrated hydrochloric acid, the solution was evaporated to dryness under reduced pressure, the residue was partitioned between a large volume of methylene chloride and a small volume of water, the methylene chloride phase was dried over magnesium sulfate and evaporated, and the residue was recrystallized from methylene chloride to give 20.3 g (75% of theory) of N-(2-naphthalenesulfonyl)-L- or D-glutamic acid as white solid. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ON1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ;m1_m2_m3_m4:Cl.N1=CC=C(C=C1)CCl, amount is: 0.0 ;m1_m2_m3_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=CC=C(C=C1)CON1C(C2=CC=CC=C2C1=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Under anhydrous conditions (positive nitrogen pressure, presence of 3Å molecular sieves), a mixture of N-hydroxyphthalimide (15.0g, 0.091mole), 4-picolylchloride hydrochloride (15.0g, 0.091mole), and triethylamine (27.7g, 0.273 mol) in 125 ml of anhydrous acetonitrile was refluxed for 2 hours. After stirring overnight at ambient temperature, TLC showed that the starting materials were practically consumed. Ethyl acetate (500 ml) was added, mixture stirred for 15 min and filtered. The solvent was evaporated and the residue dissolved in 1L of EtOAc. The filtrate was washed with water (2×500 ml), brine (1×500 ml), dried (MgSO4), and evaporated to a smaller volume (100ml). The mixture was cooled down to -18° C., precipitate filtered and recrystallized from EtOAc/hexane to afford 13.2g (56.8%) of title product. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:ON1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ;m1_m2_m3_m4:Cl.N1=C(C=CC=C1)CCl, amount is: 0.0 ;m1_m2_m3_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=C(C=CC=C1)CON1C(C2=CC=CC=C2C1=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Under anhydrous conditions (positive nitrogen pressure, presence of 3Å molecular sieves), a mixture of N-hydroxyphthalimide (10.0 g, 0.061 mole), 2-picolylchloride hydrochloride (10.0 g, 0.061 mole), and triethylamine (18.5g, 0.183 mol) in 100 ml of anhydrous acetonitrile was refluxed for 6 hours. After overnight stirring at ambient temperature, TLC showed that the starting materials were practically consumed. The solvent was evaporated and the residue dissolved in 200 ml of EtOAc. The solution was washed with 1N NaOH (100 ml), water (2×200 ml), brine (1×200 m ml) and dried (MgSO4). After removal of the solvent, the crude product was recrystallized from EtOAc/hexane to afford 11.4g (73.6%) of title product. |
Here is a chemical reaction formula: Reactants are m3:[OH-].[Na+], amount is: 0.0 MOLE;m1_m4_m2_m5:C(=O)(O)CCCC=C1C[C@@H]2CC3(C[C@@H]2C1)OCCO3, amount is: 0.0 ;m1_m4_m2_m5:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m5:O1CCCC1, amount is: 0.0 ;m1_m4_m2_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OCCCCC=C1C[C@@H]2CC3(C[C@@H]2C1)OCCO3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 49.10 g of 3-(4-carboxybutylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]octane (prepared as described in Preparation 1) in 150 ml of tetrahydrofuran were added dropwise to a suspension of 10.50 g of lithium aluminum hydride in 675 ml of tetrahydrofuran, whilst cooling with ice. The mixture was then heated under reflux for 80 minutes. Upon completion of the reaction, 42 ml of a 4% w/v aqueous solution of sodium hydroxide were added, and the mixture was stirred at room temperature. The resulting precipitate was removed by filtration, and the filtrate was condensed by evaporation under reduced pressure, giving 46.90 g of a residue. On purifying the residue by silica gel column chromatography, 40.10 g of the title compound were obtained as an oil, from the fractions eluted with hexane containing 20-30% by volume of ethyl acetate. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ;m1_m2_m3_m4:C(CO)O, amount is: 0.0 ;m1_m2_m3_m4:C(C1=CC=CC=C1)OCCCCC=C1C[C@@H]2CC3(C[C@@H]2C1)OCCO3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OCCCCCC1=C[C@@H]2CC3(C[C@@H]2C1)OCCO3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.50 g of p-toluenesulfonic acid and 2.9 ml of ethylene glycol were added to 17.8 g of 3-(5-benzyloxy-pentylidene)-7,7-ethylenedioxy-cis-bicyclo[3,3,0 ]octane (prepared as described in Preparation 3) in 300 ml of benzene, and the mixture was heated, with stirring, for 2.5 hours whilst removing water as an azeotropic mixture. Upon completion of the reaction, the reaction mixture was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off from the reaction mixture under reduced pressure, to give 18.20 g of the title compound as an oil. This mixture was used for the subsequent reaction of Preparation 5 without purification. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C(CO)O, amount is: 0.0 ;m1_m2_m3_m5:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ;m1_m2_m3_m5:C(C1=CC=CC=C1)OCCCCCC1(C[C@@H]2CC3(C[C@@H]2C1)OCCO3)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:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OCCCCCC1=C[C@@H]2CC3(C[C@@H]2C1)OCCO3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Ethylene glycol (0.05 ml) and 10 mg of p-toluenesulfonic acid were added to a solution of 209 mg of 3-(5-benzyloxypentyl)-7,7-ethylenedioxy-3-hydroxy-cis-bicyclo[3,3,0]octane (prepared as described in Preparation 9) in 2 ml of benzene, and the mixture was heated, with stirring, for 3.5 hours, whilst removing water as an azeotropic mixture. Upon completion of the reaction, the reaction mixture was neutralized with a 5% w/v aqueous solution of sodium bicarbonate. The reaction mixture was then washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off from the reaction mixture under reduced pressure, giving 193 mg of a residue. This residue was purified by silica gel column chromatography and 142 mg of the title compound were obtained as an oil from the fractions eluted with hexane containing 2-5% by volume of ethyl acetate. The product had the same properties as that of Preparation 4. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OCCC1=C[C@@H]2CC3(C[C@@H]2C1)OCCO3, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CC(=O)C, amount is: 0.0 ;m1_m2_m3_m4:O, amount is: 0.0 ;m1_m2_m3_m4:Cl, amount is: 0.0 ;m5:[Cl-].[Na+], amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:OCCC1=C[C@@H]2CC(C[C@@H]2C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 3.00 g of 3-(2-hydroxyethyl)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]oct-2-ene (prepared as described in Preparation 43) were dissolved in a mixture of 30 ml of acetone and 12 ml of water, and 0.5 ml of concentrated hydrochloric acid was added to the solution. The mixture was stirred for 1 hour at room temperature, after which it was diluted with a saturated aqueous solution of sodium chloride, and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, and the resulting residue (2.61 g) was purified by silica gel column chromatography. 1.97 g of the title compound was obtained in the form of an oil from the fractions eluted with hexane containing from 35 to 45% by volume of ethyl acetate. |
Here is a chemical reaction formula: Reactants are m1_m5_m6_m2:NC=1C(=CC=CC1)C, amount is: 1.0 MOLE;m1_m5_m6_m2:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.6499999761581421 MOLE;m3:CC(C(=O)Cl)(C)C, amount is: 1.0 MOLE;m4:CC(C(=O)Cl)(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m6_m2:C(Cl)Cl, amount is: 0.0 ;m1_m5_m6_m2:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC1=C(C=CC=C1)NC(C(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A biphasic solution of o-toluidine (107.2g, 1.0 mol) in methylene chloride (500 ml) and water (150 ml)-containing sodium carbonate (69g, 0.65 mol) was treated with trimethylacetyl chloride (120.6g, 1.0 mol). The rate of addition of trimethylacetyl chloride was adjusted so as to maintain the reaction at gentle reflux. After 45 minutes the addition was complete. The organic layer was separated, washed with water, and concentrated in vacuo. The crude N-[(2-methyl)phenyl]-2,2-dimethylpropanamide was slurried in 2% aqueous HC1, filtered and washed with H2O until the filtrate was neutral. After drying in vacuo (50° C., 20 ram), N-[(2-methyl)phenyl]-2,2-dimethylpropanamide (178 g, 0.93 mol) was obtained in 93% yield. (top 109°-110° C.). |