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Here is a chemical reaction formula: Reactants are:m3_m5:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1;m1_m4_m2:N1=CC=C2CNC3=C(CN21)C=CC=C3;m1_m4_m2:C(C)N(CC)CC, Reagents are:m3_m5:C(Cl)Cl;m1_m4_m2:C(Cl)Cl;m6:C(C)(=O)OCC, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 10 mmol of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine in 50 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 11 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, NaHCO3, and brine. The reaction mixture is dried with Na2 SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give desired product as a solid, m.p. 227°-229° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1;m1_m3_m2_m4:C(C)(=O)OCC, Reagents are:m1_m3_m2_m4:C(C)O;m1_m3_m2_m4:[Pd], and Products are 0:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5 mmol of 5,10-dihydro-5-(4-nitrobenzoyl)-4H-pyrazolo-[5,1-c][1,4]benzodiazepine in 25 ml of ethyl alcohol and 10 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a solid which is purified by flash chromatography on silica gel to give the desired product as a tan solid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4_m2:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1;m1_m3_m4_m2:NN, Reagents are:m1_m3_m4_m2:C(C)O;m1_m3_m4_m2:[Pd], and Products are 0:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5 mmol of 5,10-dihydro-5-(4-nitrobenzoyl)-4H-pyrazolo-[5,1-c][1,4]benzodiazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine. The mixture is heated under reflux for 3 hours, and the mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in methylene chloride and passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give the desired product which is purified by flash chromatography on silica gel to give the desired product as a solid, exact mass by mass spectrometry: 305. 1402 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:CC1=C(C(=O)Cl)C=CC=C1;m1_m4_m2_m3:C(C)N(CC)CC;m1_m4_m2_m3:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1, Reagents are:m1_m4_m2_m3:C(Cl)Cl, and Products are 0:N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 3 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 5 mmol of triethylamine and 3 mmol of 5,10-dihydro-5-(4-aminobenzoyl)-4H-pyrazolo-[5,1-c][1,4]benzodiazepine. The mixture is stirred at room temperature for 5 hours and is then washed with water, NaHCO3, and brine. The organic layer is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give the desired product as a solid, m.p. 142°-146° C. |
Here is a chemical reaction formula: Reactants are:m1_m4:O=C1C=2N(CC3=C(N1)SC=C3)C=CC2;m3:CO;m2_m5:[B].CSC, Reagents are:m1_m4:O1CCCC1;m2_m5:O1CCCC1, and Products are 0:S1C=CC2=C1NCC=1N(C2)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 7.0 g of 9-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepin in 25 ml of anhydrous tetrahydrofuran is added 9 ml of 10 molar boron-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours. The solution is cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum. To the residue is added 100 ml of 2N NaOH. The mixture is refluxed 5 hours and filtered. The solid is extracted with dichloromethane and the extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed in vacuo to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:S1C=CC2=C1NCC=1N(C2)C=CC1;m1_m4_m2:C(C)N(CC)CC;m3_m5:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1, Reagents are:m1_m4_m2:C(Cl)Cl;m6:C(C)(=O)OCC;m3_m5:C(Cl)Cl, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 10 mmol of 9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine in 50 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 11 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 1N HCl, NaHCO3, and brine. The organic layer is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1;m1_m3_m2_m4:C(C)(=O)OCC, Reagents are:m1_m3_m2_m4:C(C)O;m1_m3_m2_m4:[Pd], and Products are 0:NC1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2 g of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-pyrrolo-[1,2-a]thieno[2,3-e][1,4]diazepine in 20 ml of ethyl alcohol and 20 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a solid which is purified by flash chromatography to give the desired product. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4_m2:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1;m1_m3_m4_m2:NN, Reagents are:m1_m3_m4_m2:C(C)O;m1_m3_m4_m2:[Pd], and Products are 0:NC1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5 mmol of 9,10-dihydro-10-(4-nitrobenzoyl)-4H-pyrrolo-[1,2-a]thieno[2,3-e][1,4]diazepine in 25 ml of ethyl alcohol is added 0.13 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The cooled reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in methylene chloride and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give the desired product which is purified by flash chromatography on silica gel to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:CC1=C(C(=O)Cl)C=CC=C1;m1_m4_m2_m3:C(C)N(CC)CC;m1_m4_m2_m3:NC1=CC=C(C(=O)N2CC=3N(CC4=C2SC=C4)C=CC3)C=C1, Reagents are:m1_m4_m2_m3:C(Cl)Cl, and Products are 0:S1C=CC2=C1N(CC=1N(C2)C=CC1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC=C1)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 5 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 7 mmol of triethylamine and 5 mmol of 9,10-dihydro-10-(4-aminobenzoyl)-4H-pyrrolo-[1,2-a]thieno[2,3-e][1,4]diazepine and the mixture stirred for 5 hours. The reaction mixture is washed with water, 2N citric acid, NaHCO3, and brine. The organic layer is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m3_m5:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1;m1_m4_m2:S1C=CC=2NCC=3N(CC21)C=CC3;m1_m4_m2:C(C)N(CC)CC, Reagents are:m6:C(C)(=O)OCC;m3_m5:C(Cl)Cl;m1_m4_m2:C(Cl)Cl, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3 mmol of 4,10-dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine in 10 ml of methylene chloride under argon is added 5 mmol of triethylamine followed by ice bath cooling. A solution of 3.3 mmol of 4-nitrobenzoyl chloride in 3 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1;m1_m3_m2_m4:C(C)(=O)OCC, Reagents are:m1_m3_m2_m4:C(C)O;m1_m3_m2_m4:[Pd], and Products are 0:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5 mmol of 4,10-dihydro-4-(4-nitrobenzoyl)-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of ethyl alcohol and 25 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a solid which is purified by flash chromatography on silica gel to give the desired product. |
Here is a chemical reaction formula: Reactants are:m1_m3:[N+](=O)([O-])C1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1;m4_m2:NN, Reagents are:m1_m3:C(C)O;m4_m2:[Pd], and Products are 0:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 5 mmol of 4,10-dihydro-4-(4-nitrobenzoyl)-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The cooled reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in methylene chloride and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give the desired product which is purified by flash chromatography on silica gel to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:CC1=C(C(=O)Cl)C=CC=C1;m1_m4_m2_m3:C(C)N(CC)CC;m1_m4_m2_m3:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CS4)C=CC3)C=C1, Reagents are:m1_m4_m2_m3:C(Cl)Cl, and Products are 0:S1C=CC=2N(CC=3N(CC21)C=CC3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 3 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 5 mmol of triethylamine and 3 mmol of 4,10-dihydro-4-(4-aminobenzoyl)-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine. The mixture is stirred for 5 hours. The reaction mixture is washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give the desired product as a solid, m.p. 162°-188° C. (amorphous) |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:C1=CC=CC=2NCCC=3N(C21)C=CC3;m1_m4_m2:C(C)N(CC)CC;m3_m5:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1, Reagents are:m1_m4_m2:C(Cl)Cl;m3_m5:C(Cl)Cl;m6:C(C)(=O)OCC, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 10 mmol of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 30 ml of methylene chloride under argon is added 15 mmol of triethylamine followed by ice bath cooling. A solution of 11 mmol of 4-nitrobenzoyl chloride in 10 ml of methylene chloride is added dropwise. Following complete addition, the ice bath is removed and the reaction mixture stirred at room temperature for 2 hours. The volatiles are removed in vacuo to give a residue which is dissolved in ethyl acetate. The solution is washed with water, 2N citric acid, NaHCO3, and brine. The reaction mixture is dried with Na2 SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:[N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1;m1_m2_m4_m3:C(C)O, Reagents are:m1_m2_m4_m3:[Pd];m1_m2_m4_m3:C(C)(=O)OCC, and Products are 0:NC1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2.0 g of 6,7-dihydro-5-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine, 20 ml of ethyl alcohol and 20 ml of ethyl acetate containing 0.2 g of 10% Pd/C is hydrogenated for 5 hours. The reaction mixture is filtered through a pad of diatomaceous earth. The filtrate is concentrated in vacuo to a solid which is purified by flash chromatography on silica gel to give the desired product. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4_m2:[N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1;m1_m3_m4_m2:NN, Reagents are:m1_m3_m4_m2:C(C)O;m1_m3_m4_m2:[Pd], and Products are 0:NC1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5 mmol of 6,7-dihydro-5-(4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 25 ml of ethyl alcohol is added 0.3 g of 10% Pd/C and 15 mmol of hydrazine followed by stirring and heating under reflux for 3 hours. The reaction mixture is filtered through diatomaceous earth. The filtrate is concentrated in vacuo to a residue which is dissolved in methylene chloride and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give the desired product which is purified by flash chromatography on silica gel to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m2_m3:C(C)N(CC)CC;m2_m3:C1=CC=CC=2NCCC=3N(C21)C=CC3;m1_m4:CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1, Reagents are:m1_m4:C(Cl)Cl;m5:C(C)(=O)OCC, and Products are 0:C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 1.37 g (5 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride in 10 ml of methylene chloride, cooled to 0° C. is added 7 mmol of triethylamine and 5 mmol of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine. The cooling bath is removed and the reaction mixture is allowed to stir at room temperature for 48 hours. The volatiles are removed in vacuo to give a residue. The residue is dissolved in 100 ml of ethyl acetate and washed with water, 2N citric acid, aqueous NaHCO3 and brine. The solution is dried with Na2SO4 and the solvent removed in vacuo to give a solid. The solid is triturated with ether-hexane to give the desired product, mass spectrum (CI): 422(M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:CC1=C(C(=O)Cl)C=CC=C1;m1_m4_m2_m3:C(C)N(CC)CC;m1_m4_m2_m3:NC1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1, Reagents are:m1_m4_m2_m3:C(Cl)Cl, and Products are 0:C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=CC=C(C=C3)NC(C3=C(C=CC=C3)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 5 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 7 mmol of triethylamine and 5 mmol of 6,7-dihydro-5-(4-aminobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine. The reaction mixture is washed with water, 2M citric acid, NaHCO3, and brine. The organic layer is dried with Na2SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography on silica gel to give the desired product as a solid; mass spectrum (CI): 422(M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4:C1=NN=C2N1C1=C(NC(C2)=O)C=CC=C1;m3:CO;m2_m5:B.CSC, Reagents are:m1_m4:O1CCCC1;m2_m5:O1CCCC1, and Products are 0:C1=NN=C2N1C1=C(NCC2)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 7.0 g of 5,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one in 25 ml of tetrahydrofuran is added 9 ml of 10M borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours, cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum and to the residue is added 100 ml of 2N sodium hydroxide. The mixture is refluxed for 5 hours, chilled and extracted with dichloromethane. The extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed under vacuum to give a solid. The solid is purified by chromatography on silica gel to give the desired product. |
Here is a chemical reaction formula: Reactants are:m1_m4:C1=NN=C2N1C1=C(NCC2)C=CC=C1;m2:CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1;m3:C(C)N(CC)CC, Reagents are:m1_m4:ClCCl, and Products are 0:C1=NN=C2N1C1=C(N(CC2)C(=O)C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 5 mmol of 5,6-dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine in 20 ml of dichloromethane is added 5.5 mmol of 4-[(2-methylbenzoyl)amino]benzoyl chloride and then 7.5 mmol of triethylamine. The mixture is stirred at room temperature for 8 hours and then washed with water, aqueous NaHCO3 and brine. The solution is dried (Na2SO4) and the solvent removed in vacuo to give a solid. The solid is purified by chromatography on silica gel with ethyl acetate-hexane as solvent to give the desired product as a glass. |
Here is a chemical reaction formula: Reactants are:m1_m4:C1=NN=C2N1C1=C(NCC2)C=CC=C1;m2:C(C)N(CC)CC;m3_m5:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1, Reagents are:m1_m4:ClCCl;m3_m5:ClCCl, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=NN3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 3 mmol of 5,6-dihydro-4H-[1,2,4]-triazolo[4,3-a][1,5]benzodiazepine in 10 ml of dichloromethane under argon is added 5 mmol of triethylamine. To the mixture is added dropwise 3.3 mmol of 4-nitrobenzoyl chloride in 3 ml of dichloromethane. The mixture is stirred at room temperature 3 hours and then washed with water, aqueous NaHCO3 and brine. The organic layer is dried (Na2SO4) and the solvent removed under vacuum. The residue is purified by chromatography on silica gel to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m2_m3:CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1;m2_m3:C(C)N(CC)CC;m1_m4:CC1=NN=C2N1C1=C(NCC2)C=CC=C1, Reagents are:m1_m4:ClCCl, and Products are 0:CC1=NN=C2N1C1=C(N(CC2)C(=O)C2=CC=C(C=C2)NC(C2=C(C=CC=C2)C)=O)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 5 mmol of 5,6-dihydro-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine in 20 ml of dichloromethane is added 5.5 mmol of 4-[(2-methylbenzoyl)amino]benzoyl chloride and 7.5 mmol of triethylamine. The mixture is stirred at room temperature for 8 hours and then washed with water, aqueous NaHCO3 and brine. The organic layer is dried (Na2SO4) and the solvent removed in vacuo to give a solid. The solid is purified by chromatography on silica gel with ethyl acetate-hexane as solvent to give the desired product. |
Here is a chemical reaction formula: Reactants are:m1_m4:CC1=NN=C2N1C1=C(NCC2)C=CC=C1;m2_m3:ClC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC(=C1)Cl;m2_m3:C(C)N(CC)CC, Reagents are:m1_m4:ClCCl, and Products are 0:CC1=NN=C2N1C1=C(N(CC2)C(=O)C2=CC=C(C=C2)NC(C2=C(C=C(C=C2)Cl)Cl)=O)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 5 mmol of 5,6-dihydro-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine in 20 ml of dichloromethane is added 5.5 mmol of 4-[(2,4-dichlorobenzoyl)amino]benzoyl chloride and 7.5 mmol of triethylamine. The mixture is stirred at room temperature for 8 hours and then washed with water, aqueous NaHCO3 and brine. The organic layer is dried (Na2SO4) and the solvent removed in vacuo to give a solid. The solid is purified by chromatography on silica gel to give the desired product as a solid. |
Here is a chemical reaction formula: Reactants are:m2:[OH-].[Na+];m1_m3:CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)OCC)C=C1, Reagents are:m1_m3:CO, and Products are 0:CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A sample of 1.51 g of sodium hydride (60% in oil) is washed with hexane under argon to remove the oil. To the washed sodium hydride is added 5 ml of N,N-dimethylformamide. To this mixture is added dropwise a solution of 8.69 g of ethyl 4-[(2-methylbenzoyl)amino]benzoate in 20 ml of N,N-dimethylformamide. The mixture is stirred at room temperature for 0.5 hour and then 5.23 g of methyl iodide is added. The mixture is stirred at room temperature for 16 hours. The mixture is diluted with water and extracted with dichloromethane. The extract is dried (Na2SO4), concentrated to reduce the volume and the solution filtered through a thin pad of hydrous magnesium silicate. The filtrate is concentrated in vacuo to give 11 g of an oil (1:1 mixture of product and N,N-dimethylformamide). The preceding product, ethyl 4-[N-methyl-N-(2-methylbenzoyl)amino]benzoate, (11 g) is dissolved in 30 ml of methanol and 25 ml of 2N NaOH added. The mixture is refluxed for 2 hours and the solvent removed. The residue is extracted with ether (discard) and the remaining residue dissolved in 50 ml of water. The basic solution is acidified with 2N citric acid and the solid filtered off and washed with water. The product is air dried to give 6.72 g of crystals, m.p. 187°-190° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C=1C=CN2C1CNC1=C(C2)C=CC=C1;m1_m2_m3_m4:CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)Cl)C=C1;m1_m2_m3_m4:C(C)N(CC)CC;m1_m2_m3_m4:O1CCCC1;m5_m6_m7:CN(C(C1=C(C=CC=C1)C)=O)C1=CC=C(C(=O)Cl)C=C1;m5_m6_m7:C(C)N(CC)CC, Reagents are:m8:O;m5_m6_m7:ClCCl, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)N(C(C1=C(C=CC=C1)C)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.27 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0,518 g of 4-[N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride, 0.182 g of triethylamine and 7 ml of tetrahydrofuran is stirred at room temperature for 3 hours. To the mixture is added 0.29 g of 4-[N-methyl-N-(2-methylbenzoyl)amino]benzoyl chloride and 0.10 g of triethylamine in 2 ml of dichloromethane and the mixture stirred for 2 days. The mixture is poured into water and extracted with dichloromethane. The extract is washed with water, 1N HCl, 1N NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate. The filtrate is evaporated in vacuo and the residue crystallized from dichloromethane-hexane to give 0.38 g of crystals, m.p. 168°-170° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC=1C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC1N;m1_m2_m3_m4:ClC1=C(C(=O)Cl)C=CC(=C1)Cl;m1_m2_m3_m4:C(C)(C)N(CC)C(C)C, Reagents are:m1_m2_m3_m4:ClCCl, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.40 g of 10,11-dihydro-10-(3-methyl-4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.40 g of 2,4-dichlorobenzoyl chloride and 0.75 g of diisopropylethylamine in 50 ml of dichloromethane is stirred at room temperature for 16 hours. The mixture is washed with water, dried (MgSO4) and the solution passed through a thin pad of hydrous magnesium silicate. The filtrate is concentrated and hexane added to give crystals. Recrystallization from dichloromethane-hexane gives 0.52 g of crystals, m.p. 213°-215° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:N1C(CCNC2=C1C=CC=C2)=S;m1_m2_m3:C(=O)NN, Reagents are:m1_m2_m3:C(CCC)O, and Products are 0:C1=NN=C2N1C1=C(NCC2)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-thione (0.8 g) and 0.80 g of N-formylhydrazine in 8 ml of n-butanol is stirred and refluxed for 18 hours and the solvent removed under vacuum. Ice water is added to the residual solid and the mixture filtered to give 0.312 g of a gray solid, m.p. 162°-165° C. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m5:[N+](=O)([O-])C1=C(C=CC=C1)N1C(=CC=C1)CC(=O)OCC;m1_m4_m2_m5:O.O.[Cl-];m3:C([O-])([O-])=O.[Na+].[Na+], Reagents are:m1_m4_m2_m5:C(C)O;m1_m4_m2_m5:Cl, and Products are 0:C1=CC=CC=2NC(CC=3N(C21)C=CC3)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0.8 mmol of 1-(2-nitrophenyl)-2-pyrroleacetic acid, ethyl ester in 3 ml of ethanol is added stannus chloride dihydrate (SnCl2.2H2O) in 2 ml of concentrated hydrochloric acid (with cooling in water bath). The mixture is stirred at room temperature for 5 hours and chilled in an ice bath. To the mixture is added slowly saturated sodium carbonate solution. The solid which precipitates is filtered and the solid washed with water and then extracted with ethyl acetate. The ethyl acetate extract is dried (Na2SO4) and the solvent removed to give 0.16 g of solid which is triturated with ether to give 0.11 g of product as an off-white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:FC=1C=CC(=C(C(=O)NC2=CC=C(C(=O)OCC)C=C2)C1)C;m1_m2_m3_m4:[OH-].[Na+];m1_m2_m3_m4:O;m1_m2_m3_m4:C(C)O, Reagents are:m5:C(C)(=O)O, and Products are 0:FC=1C=CC(=C(C(=O)NC2=CC=C(C(=O)O)C=C2)C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.60 g of ethyl 4-[(5-fluoro-2-methylbenzoyl)amino]benzoate 0.60 ml of 10N NaOH, 25 ml of water and 50 ml of absolute ethyl alcohol is heated on a steam bath for 1 hour, cooled and acidified with acetic acid. The resulting solid is filtered and dried in vacuo at 60°-80° C. to give 0.47 g of the desired product as a solid, m.p. 272°-275° C. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m5:ClC1=C(C(=O)O)C=CC(=C1)N;m2_m3:C(C)(C)N(C(C)C)CC;m2_m3:ClC1=C(CCl)C=CC(=C1)Cl, Reagents are:m1_m5:C(Cl)Cl, and Products are 0:ClC1=C(C(=O)NC2=CC(=C(C(=O)O)C=C2)Cl)C=CC(=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred mixture of 5.19 g of 2-chloro-4-aminobenzoic acid in 150 ml of methylene chloride is added 7.86 g of N,N-diisopropylethylamine and 12.67 g of 2,4-dichlorobenzylchloride and stirring continued for 18 hours. Water is added to the filtrate and the organic layer dried with Na2 SO4 and concentrate in vacuo to give 13.68 g of the desired product, m.p. 171°-175° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:COC=1C=C(C(=O)O)C=CC1[N+](=O)[O-];m1_m2:S(=O)(Cl)Cl, Reagents are:, and Products are 0:COC=1C=C(C(=O)Cl)C=CC1[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5.0 g of 3-methoxy-4-nitrobenzoic acid and 5.0 g of thionyl chloride is heated under argon for 1 hour. The volatiles are removed in vacuo to give 2.85 g of a 3-methoxy-4-nitrobenzoyl chloride as a residue which is dissolved in 50 ml of methylene chloride. To the preceding solution is added with stirring 1.75 g of N,N-diisopropylethylamine followed by 1.84 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine. The reaction mixture is stirred under argon for 18 hours and diluted with saturated sodium bicarbonate. The organic layer is dried with Na2 SO4 and passed through a short pad of hydrous magnesium silicate. While boiling, hexane is added to the filtrate to give, upon cooling, 3.39 g of the desired product as a solid, m.p. 191°-192° C. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:[N+](=O)([O-])C1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC;m1_m4_m2_m3:NN, Reagents are:m1_m4_m2_m3:C(C)O;m1_m4_m2_m3:[Pd], and Products are 0:NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 3.24 g of 10,11-dihydro-10-(4-nitro-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.35 g of 10% Pd/c and 0.60 g of anhydrous hydrazine in 100 ml of absolute ethyl alcohol and heated on a steam bath for 1 hour. The hot reaction mixture is filtered through diatomaceous earth and the filtrate evaporated in vacuo to a residue which is partitioned between methylene chloride and water. The organic layer is dried with Na2SO4 and passed through a short pad of hydrous magnesium silicate. Hexane is added to the filtrate while heating on a steam bath to give 2 g of crystals, m.p. 184°-185° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)N(CC)CC;m1_m4:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1;m3_m5:CC1=C(C(=O)Cl)C=C(C=C1)F, Reagents are:m1_m4:C(Cl)Cl;m3_m5:C(Cl)Cl, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=CC(=C1)F)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 3 ml of methylene chloride, cooled to 0° C., under argon, is added 346 μl of triethylamine followed by the addition of 340 mg of 2-methyl-5-fluorobenzoyl chloride in 2 ml of methylene chloride. The cooling bath is removed and stirring continued for 18 hours. After cooling to 0° C., an additional 342 mg of 2-methyl-5-fluorobenzoyl chloride in 2 ml of methylene chloride is added. The cooling bath is removed and stirring continued for 18 hours. The volatiles are removed in vacuo to a residue which is dissolved in 50 ml of methylene chloride and washed with 20 ml each of water, 2N citric acid, 1M sodium bicarbonate and brine. The organic layer is dried over Na2SO4 and passed through a pad of hydrous magnesium silicate. The filtrate is evaporated in vacuo to a residue which is crystallized from ethyl acetate-hexane to give 295 mg of the desired product as a white solid, m.p. 170°-180° C. |
Here is a chemical reaction formula: Reactants are:m4:O;m3_m6:CC1=C(C(=O)NC2=CC(=C(C(=O)Cl)C=C2)Cl)C=C(C=C1)F;m1_m5_m2:C=1C=CN2C1CNC1=C(C2)C=CC=C1;m1_m5_m2:C(C)(C)N(C(C)C)CC, Reagents are:m3_m6:C(Cl)Cl;m1_m5_m2:C(Cl)Cl, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=C(C=C(C=C1)NC(C1=C(C(=CC=C1)F)C)=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.50 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 25 ml of methylene chloride is added 1.23 g of N,N-diisopropylethylamine. While cooling in an ice bath, a solution of 3.08 g of [4-[(2-methyl-5-fluorobenzoyl)amino]-2-chlorobenzoyl chloride in 50 ml of methylene chloride is added. The reaction mixture becomes homogeneous and is stirred at room temperature for 18 hours. Water is added and the separated organic layer washed with saturated sodium bicarbonate, dried with Na2SO4 and passed through a short pad of hydrous magnesium silicate two times. The methylene chloride is removed in vacuo to give 3.81 g of a glass. A sample is crystallized from ethyl acetate to give crystalline solid, m.p. 200°-205° C. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:C=1C=CN2C1CNC1=C(C2)C=CC=C1;m1_m5_m2:C(C)(C)N(C(C)C)CC;m3_m6:CC1=C(C(=O)NC2=CC(=C(C(=O)Cl)C=C2)Cl)C=C(C=C1)F;m4:O, Reagents are:m1_m5_m2:C(Cl)Cl;m3_m6:C(Cl)Cl, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=C(C=C(C=C1)NC(C1=C(C=CC(=C1)F)C)=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.84 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 25 ml of methylene chloride is added 1.30 g of N,N-diisopropylethylamine. While cooling in an ice bath, a solution of 3.45 g of [4-[(2-methyl-5-fluorobenzoyl)amino]-2-chlorobenzoyl chloride in 50 ml of methylene chloride is added. The reaction mixture becomes homogeneous after 5 minutes and is stirred at room temperature for 18 hours. Water is added and the separated organic layer washed with saturated sodium bicarbonate, dried with Na2SO4 and passed through a short pad of hydrous magnesium silicate. The methylene chloride is removed in vacuo to give 4.60 g of the desired product as a glass. A sample is crystallized from ethyl acetate to give crystalline solid, m.p. 191°-195° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C(=O)O)C=C1;m1_m2_m3_m4_m5:C(C)N(CC)CC;m1_m2_m3_m4_m5:NC=1C(=CC=CC1)C;m1_m2_m3_m4_m5:C(C)P(=O)(CC)C#N, Reagents are:m1_m2_m3_m4_m5:ClCCl, and Products are 0:CC1=C(C=CC=C1)NC(C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.332 g of 4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)benzoic acid, 0.111 g of triethylamine, 0.107 g of o-toluidine, and 0.15 ml of diethylphosphoryl cyanide in 20 ml of dichloromethane is heated on a steam bath overnight. The mixture is washed with water, 1M NaHCO3, 1N HCl, brine and dried (Na2SO4). The dichloromethane solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is crystallized from dichloromethane-hexane to give 0.23 g of white crystals, m.p. 228°-231° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C(=O)O)C=C1;m1_m2_m3_m4_m5:C(C)N(CC)CC;m1_m2_m3_m4_m5:Cl.CC1=C(N)C=CC=C1C;m1_m2_m3_m4_m5:C(C)P(=O)(CC)C#N, Reagents are:m1_m2_m3_m4_m5:ClCCl, and Products are 0:CC1=C(C=CC=C1C)NC(C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.332 g of 4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)benzoic acid, 0.222 g of triethylamine, 0.157 g of 2,3-dimethylaniline hydrochloride, 0.15 ml of diethylphosphoryl cyanide in 20 ml of dichloromethane is heated on a steam bath for 3 hours. The mixture is washed with H2O, 1M NaHCO3, H2O, 1N HCl, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated to dryness under vacuum and the residue crystallized from dichloromethane-hexane to give 0.11 g of crystals, m.p. 239°-240° C. |
Here is a chemical reaction formula: Reactants are:m3_m6:ClC1=C(C(=O)Cl)C=CC=C1Cl;m4:C(C)N(CC)CC;m5:ClC1=C(C(=O)Cl)C=CC=C1Cl;m1:NC1=CC=C(C(=O)N2CC=3N(C4=CC=CC=C24)C=CC3)C=C1;m2:C(C)N(CC)CC, Reagents are:m8:ClCCl;m3_m6:ClCCl;m7:ClCCl, and Products are 0:C1=CC=C2N1C1=CC=CC=C1N(C2)C(=O)C2=CC=C(C=C2)NC(C2=C(C(=CC=C2)Cl)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: As described for Example 157, 0.47 g of 4,5-dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline, 346 μl of triethylamine and 5 ml of dichloromethane are chilled (ice bath) and 0.415 g of 2,3-dichlorobenzoyl chloride in 2 ml of dichloromethane added. After stirring overnight, an additional 346 μl of triethylamine is added and an additional 0.415 g of 2,3-dichlorobenzoyl chloride added. The mixture is stirred for 2 hours, diluted with 50 ml of dichloromethane and the solution washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as solvent to give 0.100 g of white solid, m.p. 230°-240° C. |
Here is a chemical reaction formula: Reactants are:m2_m3:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1;m2_m3:C(C)N(CC)CC;m1_m4:ClC1=C(C=CC=C1)S(=O)(=O)Cl, Reagents are:m5:ClCCl;m1_m4:ClCCl, and Products are 0:ClC1=C(C=CC=C1)S(=O)(=O)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0,418 g of 2-chlorobenzenesulfonyl chloride in 5 ml of dichloromethane, cooled to 0° C. is added 0.50 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 0.346 μl of triethylamine. The mixture is stirred at room temperature overnight and diluted with 50 ml of dichloromethane. The mixture is washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is chromatographed on thick layer silica gel plates (4) with the solvent ethyl acetate-hexane (1:1) to give a solid. Crystallization from ethyl acetate gives 0.165 g of white crystals, m.p. 206°-210° C. |
Here is a chemical reaction formula: Reactants are:m3:[I-].CC=[N+]=CC;m1_m4_m2:[H-].[Na+];m1_m4_m2:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O;m1_m4_m2:O1CCCC1, Reagents are:m5:C(C)OCC, and Products are 0:CN(C)CN(C(C1=C(C=C(C=C1)Cl)Cl)=O)C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension under argon of 0.072 g of sodium hydride (60% in oil) in 10 ml of tetrahydrofuran is added 0.71 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2,4-dichlorobenzamide and the mixture stirred at room temperature for 1 hour. To the mixture is added N,N-dimethylmethyleneammonium iodide and the mixture stirred 20 hours. The mixture is diluted with diethyl ether (30 ml), filtered and the filtrate concentrated under vacuum. The residue is triturated with hexane to give 0.76 g of white solid, m.p. 126°-129° C. |
Here is a chemical reaction formula: Reactants are:m4:[OH-].[Na+];m1_m2_m3_m5:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1;m1_m2_m3_m5:C(C)N(CC)CC;m1_m2_m3_m5:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl, Reagents are:m1_m2_m3_m5:ClCCl, and Products are 0:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.10 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine 0.060 g of triethylamine and 0.12 g of diphenylphosphinyl chloride in 2 ml of dichloromethane is stirred at room temperature for 2 hours and then 1N NaOH is added. The mixture is extracted with ethyl acetate and the extract washed with brine and dried (Na2SO4). The solvent is removed and the residue triturated with ether-hexane to give 0.16 g of a white solid. |
Here is a chemical reaction formula: Reactants are:m6:[OH-].[Na+];m4_m5:ClC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl;m4_m5:C(C)N(CC)CC;m1_m2_m3_m7:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1;m1_m2_m3_m7:C(C)N(CC)CC;m1_m2_m3_m7:ClC1=C(C=C(C=C1)Cl)S(=O)(=O)Cl, Reagents are:m1_m2_m3_m7:ClCCl;m8:CN(C)C1=CC=NC=C1, and Products are 0:ClC1=C(C=C(C=C1)Cl)S(=O)(=O)NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.10 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 0.050 g of triethylamine and 0.083 g of 2,5-dichlorobenzenesulfonyl chloride in 2 ml of dichloromethane is stirred at room temperature for 1 hour and then 4 mg of 4-(N,N-dimethylamino)pyridine is added. After another hour, 93 mg of 2,5-dichlorobenzenesulfonyl chloride is added along with 50 mg of triethylamine. The mixture is stirred at room temperature for 2 days and 1N NaOH added. The mixture is extracted with ethyl acetate and the extract washed with 50% ammonium chloride solution, brine and dried (Na2SO4). The solvent is removed to give 0.30 g of solid. Trituration with ether-hexane gives 0.26 g of solid. This solid is dissolved in a mixture of 5 ml of tetrahydrofuran, 1 ml of methanol, 1 ml of 1N NaOH and the mixture stirred for 18 hours at room temperature. The organic solvents are removed and the mixture extracted with ether acetate. The extract is washed with NaHCO3, brine and dried (Na2 SO4). The solvent is removed and the residue (0.16 g) triturated with ether to give 0.14 g of yellow solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:NC1=CC=C(C(=O)OCC)C=C1;m1_m2_m3:ClN1C(CCC1=O)=O, Reagents are:m1_m2_m3:ClCCl, and Products are 0:ClC=1C=C(C(=O)OCC)C=CC1N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 8.26 g of ethyl 4-aminobenzoate, 8.26 g of N-chlorosuccinimide in 50 ml of dichloromethane is refluxed overnight. The mixture is washed with saturated NaHCO3 solution and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated and hexane added. Chilling gives 7.38 g of ethyl 3-chloro-4-aminobenzoate, m.p. 82°-83° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:FC=1C(=C(C(=O)O)C=CC1)C;m1_m2:S(=O)(Cl)Cl, Reagents are:, and Products are 0:FC=1C(=C(C(=O)Cl)C=CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2.87 g of 3-fluoro-2-methylbenzoic acid in 25 ml of thionyl chloride is refluxed for 1.75 hour and the excess thionyl chloride removed under vacuum. To the residue is added toluene (several times) and the toluene removed under vacuum after each addition to give 3-fluoro-2-methylbenzoyl chloride. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3_m5:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)N=CC3)C=C1;m1_m2_m4_m3_m5:C(C)N(CC)CC;m1_m2_m4_m3_m5:FC=1C(=C(C(=O)Cl)C=CC1)C, Reagents are:m1_m2_m4_m3_m5:ClCCl;m1_m2_m4_m3_m5:ClCCl, and Products are 0:N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=CC=C(C=C3)NC(C3=C(C(=CC=C3)F)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0.25 g of 5,10-dihydro-5-(4-aminobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepine and 0.0914 g of triethylamine in 6 ml of dichloromethane under argon is added a solution of 0.156 g of 3-fluoro-2-methylbenzoyl chloride in 1.5 ml of dichloromethane. The mixture is stirred overnight at room temperature and is washed with H2O and saturated NaHCO3. The organic layer is treated with activated carbon and filtered through magnesium sulfate. The filtrate is evaporated, ethyl acetate added and the solvent removed to give 0.38 g of white crystals, m.p. 245°-250° C.: Exact mass by mass spectrometry--441.1720(M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:N1=CC=C2CNC3=C(CN21)C=CC=C3;m1_m2_m3_m4:ClC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC(=C1)Cl;m1_m2_m3_m4:C(C)(C)N(CC)C(C)C;m1_m2_m3_m4:ClCCl, Reagents are:, and Products are 0:N1=CC=C2CN(C3=C(CN21)C=CC=C3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C=C(C=C3)Cl)Cl)=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: As described for Example 518, a mixture of 0.185 g of 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine, 0.472 g of 4-[(2,4-dichlorobenzoyl)amino]benzoyl chloride and 0.158 g of diisopropylethylamine in 10 ml of dichloromethane is stirred at room temperature overnight to give the product (0.27 g) as a pale yellow glass; anal. calc'd: C, 58.7; H, 3.4; N, 11.0; Cl, 20.8 Found C, 57.3; H, 3.3; N, 9.5; Cl, 21.3. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:C=1C=CN2C1CNC1=C(C2)C=CC=C1;m1_m2_m4:C(C)(C)N(C(C)C)CC;m3_m5:CC1=C(C(=O)NC2=C(C=C(C(=O)Cl)C=C2)Cl)C=CC=C1, Reagents are:m1_m2_m4:ClCCl;m3_m5:ClCCl, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC(=C(C=C1)NC(C1=C(C=CC=C1)C)=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 1.38 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine, 1.11 g of N,N-diisopropylethylamine in 50 ml of dichloromethane is added 2.61 g of 4-[(2-methylbenzoyl)amino]-3-chlorobenzoyl chloride in 25 ml of dichloromethane. The mixture is stirred at room temperature overnight and then washed with H2O and saturated NaHCO3. The organic layer is dried (Na2SO4) and passed through a pad of hydrous magnesium silicate. The filtrate is concentrated, the residue (4.0 g) dissolved in dichloromethane and again filtered through a pad of hydrous magnesium silicate. The filtrate is evaporated to give the product as a glass (3.62 g). A 1.8 g sample of the glass is crystallized from ethyl acetate to give 1.4 g of crystals, m.p. 176°-178° C. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1;m1_m4_m2:C(C)N(CC)CC;m3:ClC(C(=O)Cl)C1=CC=CC=C1, Reagents are:m1_m4_m2:C(Cl)Cl;m6:C(=O)(O)[O-].[Na+];m5:C(Cl)Cl, and Products are 0:ClC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0.61 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.47 g of (±)-2-chloro-2-phenylacetyl chloride in 2 ml of methylene chloride. The mixture is stirred at room temperature for 1 hour and then diluted with 10 ml of 50% NaHCO3. The methylene chloride is evaporated and the residue is extracted with ethyl acetate. The separated organic layer is washed with saturated NaHCO3 and brine and then dried with Na2SO4 followed by filtering through a pad of hydrous magnesium silicate. The filtrate is evaporated to a residue which is stirred with ether-hexane to give 0.98 g of pink solid. MS(CI): 456(M+H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3_m4:ClC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2;m1_m2_m5_m3_m4:Cl.CN(CCS)C;m1_m2_m5_m3_m4:C(C)N(CC)CC;m1_m2_m5_m3_m4:CN1C(N(CCC1)C)=O, Reagents are:m1_m2_m5_m3_m4:CO, and Products are 0:CN(CCSC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.14 g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide, 0.47 g of 2-dimethylaminoethanethiol hydrochloride in 2 ml of methyl alcohol, 0.30 g of triethylamine and 3 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is heated at 60° C. for 48 hours. The methyl alcohol is evaporated and the residue diluted with water. The resulting suspension is filtered and the precipitate washed with water. The solid is dissolved in ethyl acetate and washed with saturated NaHCO3, brine and dried with Na2SO4. The mixture is filtered and the filtrate evaporated in vacuo to a residue which is stirred with ether-hexane to give 0.15 g of beige solid. MS(CI): 525(M+H). |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m3:ClC(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2;m1_m5_m2_m3:CNC;m1_m5_m2_m3:CN1C(N(CCC1)C)=O;m4:C(C)(=O)OCC.CCCCCC, Reagents are:m1_m5_m2_m3:CO, and Products are 0:CN(C(C(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2)C2=CC=CC=C2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A partial solution of ?? g of α-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]benzeneacetamide in 1 ml of methanol is treated with 0.5 ml of dimethylamine and 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and stirring continued for 20 hours. The methanol is evaporated and the residue diluted with water. The resulting solid is washed with water, dissolved in ethyl acetate and the organic layer washed with saturated NaHCO3, brine and dried with Na2SO4. The mixture is filtered and the filtrate evaporated in vacuo to give a residue which is stirred with ethyl acetate-hexane to give 0.15 g of a beige solid. MS(CI): 465 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m6:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1;m1_m4_m2_m6:C(C)N(CC)CC;m3_m5:ClCC(=O)Cl, Reagents are:m1_m4_m2_m6:C(Cl)Cl;m1_m4_m2_m6:CN(C)C1=NC=CC=C1;m3_m5:C(Cl)Cl, and Products are 0:ClCC(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 0.91 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]-benzodiazepine in 10 ml of methylene chloride is added 0.46 g of triethylamine and 36 mg of dimethylaminopyridine followed by the slow addition of 0.42 g of chloroacetyl chloride in 5 ml of methylene chloride. The resulting mixture is stirred at room temperature for 3 hours then partitioned with 10 ml of 50% NaHCO3 and the methylene chloride evaporated in vacuo. The remaining suspension is filtered, washed with 50% NaHCO3, H2O, EtOAc (2×2 ml), ether (2×5 ml) and dried in vacuo to give 1.14 g of beige solid. MS(CI): 380(M+H). |
Here is a chemical reaction formula: Reactants are:m3:CN1C(N(CCC1)C)=O;m1_m4:ClCC(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2;m2:N1CCOCC1, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1CCOCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred suspension of 0.19 g of 2-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]acetamide in 1 ml of methylene chloride is added 0.44 g of morpholine followed by 1 ml of 1,3-di-methyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and stirring continued for 20 hours. The methylene chloride is evaporated and the residue diluted with water. The resulting suspension is filtered and the precipitate washed with water. The brown solid is dissolved in 15 ml of ethyl acetate and washed with saturated NaHCO3, brine and dried with Na2SO4. The mixture is filtered and the filtrate evaporated in vacuo to give 0.23 g of a colorless gum which is stirred with ethyl acetate-hexanes to give 0.21 g of white solid. MS(CI): 431(M+H). |
Here is a chemical reaction formula: Reactants are:m3_m4:C1=CC=C(C(=C1)CBr)Cl;m3_m4:[H-].[Na+];m1_m2_m5:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1CCOCC1)=O;m1_m2_m5:C1=CC=C(C(=C1)CBr)Cl, Reagents are:m1_m2_m5:C(C)#N;m6:O, and Products are 0:ClC1=C(C=CC=C1)CN(C(CN1CCOCC1)=O)C1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.11 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-4-morpholineacetamide, 56 mg of O-chlorobenzyl bromide and 0.41 g of K2 CO3 in 5 ml of acetonitrile is heated at reflux for 18 hours. An additional 30 mg of O-chlorobenzyl bromide and 0.4 mmol of sodium hydride is added followed by heating for 24 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried with Na2SO4 and evaporated to give 0.18 g of a residue which is purified by chromatography on silica gel with 1:1 ethyl acetate-methylene chloride to give 80 mg of off white solid. MS(CI): 555 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C(=CC3)C(=O)OCC)C=C1)C;m1_m4_m2_m3:C(C)(C)N(C(C)C)CC;m1_m4_m2_m3:ClC1=C(C(=O)Cl)C=CC(=C1)Cl, Reagents are:m1_m4_m2_m3:C(Cl)Cl, and Products are 0:ClC1=C(C(=O)NC2=C(C=C(C(=O)N3CC=4N(CC5=C3C=CC=C5)C(=CC4)C(=O)OCC)C=C2)C)C=CC(=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0.30 g of ethyl 10,11-dihydro-10-(4-amino-3-methylbenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylate in 20 ml of methylene chloride is added 0.15 g of N,N-diisopropylethylamine and 0.24 g of 2,4-dichlorobenzoyl chloride. The reaction mixture is stirred at room temperature for 18 hours and washed with water, saturated NaHCO3 and dried with Na2SO4. The organic layer is passed through a pad of hydrous magnesium silicate. Hexane is added to the filtrate at the boil to give 0.24 g of solid, m.p. 174°-184° C. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1;m2:ClC1=C(C(=O)Cl)C=C(C=C1Cl)Cl, Reagents are:, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C(=CC(=C1)Cl)Cl)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: As described for Example 8, 0.50 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is reacted with 0.483 g of 2,3,5-trichlorobenzoyl chloride to give a glass which is crystallized from ethyl acetate to give 0.686 g of crystals, m.p. 231°-234° C. |
Here is a chemical reaction formula: Reactants are:m2:O1C(CCC1)C(=O)Cl;m1:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1, Reagents are:, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(=O)C1OCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: As described for Example 8, 0.500 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is reacted with 0.267 g of tetrahydrofurane-2-carbonyl chloride to give a glass which is crystallized from ethyl acetate to give 0.22 g of crystals, m.p. 208°-214° C. |
Here is a chemical reaction formula: Reactants are:m3_m6:[N+](=O)([O-])C1=C(C=C(C(=O)OCC)C=C1)CBr;m1_m4_m2_m5:[H-].[Na+];m1_m4_m2_m5:N1C(=CC=C1)C=O, Reagents are:m3_m6:O1CCCC1;m1_m4_m2_m5:O1CCCC1;m1_m4_m2_m5:O1CCCC1, and Products are 0:[N+](=O)([O-])C1=C(CN2C(=CC=C2)C=O)C=C(C=C1)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred slurry of 2.2 g of sodium hydride (60% in oil, washed with hexane) in tetrahydrofuran is added at 0° C. a solution of 4.5 g of pyrrole-2-carboxaldehyde in 25 ml of tetrahydrofuran. After the addition is complete, a solution of 15 g of ethyl 4-nitro-3-bromomethylbenzoate in 30 ml of dry tetrahydrofuran is slowly added under nitrogen. The reaction mixture is stirred at 20° C. for 8 hours and carefully quenched with water. The reaction mixture is extracted with chloroform which is washed with water, dried with Na2SO4 and concentrated in vacuo to give 12 g of the desired product as a solid; mass spectrum (M+ H)349. |
Here is a chemical reaction formula: Reactants are:m1_m4:C=1C=CN2C1CNC1=C(C2)C=C(C=C1)C(=O)OCC;m3:CC1=C(C(=O)NC2=CC=C(C(=O)Cl)C=C2)C=CC=C1;m2:C(C)N(CC)CC, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:CC1=C(C(=O)NC2=CC=C(C(=O)N3CC=4N(CC5=C3C=CC(=C5)C(=O)OCC)C=CC4)C=C2)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.2 g of ethyl 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-7-carboxylate in 100 ml of methylene chloride is cooled to 0° C. and 10 ml of triethylamine added followed by 1.5 g of 4-[(2-methylbenzoyl)amino)benzoyl chloride. The reaction mixture is stirred at room temperature for 18 hours and concentrated in vacuo to a residue which is partitioned between water and chloroform. The organic layer is dried over Na2SO4 and concentrated in vacuo to a residue. The residue is purified by column chromatography on silica gel by elution with 40% ethyl acetatehexane to give 1.0 g of the desired product as a solid; mass spectrum (M+ H)494. |
Here is a chemical reaction formula: Reactants are:m3_m5:ClC1=C(C(=O)Cl)C=CC(=C1)Cl;m1_m4:NC1=CC=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CN3)C=C1;m2:[H-].[Na+], Reagents are:m6:O1CCOCC1;m3_m5:O1CCOCC1;m1_m4:O1CCOCC1, and Products are 0:N=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(C1=C(C=C(C=C1)Cl)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of 0.330 g of 10,11-dihydro-10-(4-aminobenzoyl)-5H-imidazo[2,1-c][1,4]benzodiazepine in 15 ml of dioxane is stirred and warmed slightly to obtain a nearly complete solution. The reaction mixture is cooled to room temperature and 43 mg of sodium hydride in oil added. The mixture is warmed slightly. Gas evolution stops in a few minutes. The reaction mixture is cooled to room temperature and 153 μl of 2,4-dichlorobenzoyl chloride in 2.5 ml of dioxane added. An additional 3.5 ml of dioxane is added and the reaction mixture stirred at room temperature for 2 days. The volatiles are evaporated in vacuo to a residue which is partitioned between water and chloroform. The organic layer is separated and the aqueous phase extracted with chloroform two more times. The combined organic layers are trated with activated carbon and filtered through MgSO4. The filtrate is evaporated in vacuo to a tan foam which is purified by flash chromatography on silica gel by elution with CHCl3 and 3-7% CH3 OH in chloroform to give 310 mg of tan foam. |
Here is a chemical reaction formula: Reactants are:m3:ClC1=C(C(=O)Cl)C=CC(=C1)[N+](=O)[O-];m1_m4_m2:C1=CC=CC=2NCCC=3N(C21)C=CC3;m1_m4_m2:C(C)N(CC)CC, Reagents are:m5:C(Cl)Cl;m1_m4_m2:C(Cl)Cl, and Products are 0:ClC1=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=CC(=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0.28 g of 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 6 ml of methylene chloride is added 0.30 g of triethylamine followed by 0.50 g of 2-chloro-4-nitrobenzoyl chloride in 0.5 ml of methylene chloride. The reaction mixture is stirred at room temperature for 1 hour then quenched with 5 ml of saturated NaHCO3. The methylene chloride is evaporated in vacuo and the residue is diluted with 5 ml of water and extracted with 20 ml of ethyl acetate. The organic layer is separated washed with saturated NaHCO3 and brine, dried with Na2SO4 and evaporated in vacuo to give 0.59 g of a yellow foam which is triturated with ether-hexanes to give 0.56 g of the desired product as off-white solid. MS(CI): 368(M+H)(Cl35) 370 (M+H) (Cl37) |
Here is a chemical reaction formula: Reactants are:m1_m3_m4_m2:ClC1=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=CC(=C1)[N+](=O)[O-];m1_m3_m4_m2:O.O.Cl[Sn]Cl, Reagents are:m1_m3_m4_m2:C(C)O;m1_m3_m4_m2:O1CCCC1, and Products are 0:NC1=CC(=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0,50 g of 6,7-dihydro-5-(2-chloro-4-nitrobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine in 10 ml of ethyl alcohol and 2 ml of tetrahydrofuran is added 2.35 g of SnCl2.2H2O and the mixture stirred at 55° C. for 30 minutes. The solvents are evaporated in vacuo to a residue which is stirred with 20 ml of 1N NaOH and 40 ml of ethyl acetate for 15 minutes and filtered through diatomaceous earth. The filter pad is washed with 2×10 ml of ethyl acetate and the combined extracts washed with brine, dried (Na2SO4) and evaporated in vacuo to give 0.47 g of solid residue which is triturated with ether-hexane to give 0.43 g of light yellow crystalline solid. MS(CI): 338 (M+H, Cl35) 340 (M+H, Cl37) |
Here is a chemical reaction formula: Reactants are:m3_m6:FC=1C(=C(C(=O)Cl)C=CC1)C;m4:[OH-].[Na+];m1_m2_m5:NC1=CC(=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1)Cl;m1_m2_m5:C(C)N(CC)CC, Reagents are:m3_m6:ClCCl;m1_m2_m5:ClCCl, and Products are 0:C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C(=CC=C3)F)C)=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo-[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.08 g of 3-fluoro-2-methylbenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred for 2 hours at room temperature and then 2 ml of 1N NaOH added. The volatiles are evaporated under vacuum and the residue dissolved in 2 ml of tetrahydrofuran and 1 ml of methanol. The mixture is stirred for 2 hours and evaporated and the residue diluted with 2 ml of i N NaOH and 5 ml of water. The mixture is extracted with ethyl acetate (15 ml) and the extract washed with brine and dried (Na2SO4). The solvent is removed and the residue triturated with diethyl ether-hexane to give 0.15 g of white solid: Mass Spectrum (CI)474(M+H, Cl35); 476(M+H, Cl37). |
Here is a chemical reaction formula: Reactants are:m3_m6:ClC1=C(C(=O)Cl)C=CC(=C1)Cl;m1_m2_m5:NC1=CC(=C(C(=O)N2CCC=3N(C4=C2C=CC=C4)C=CC3)C=C1)Cl;m1_m2_m5:C(C)N(CC)CC;m4:[OH-].[Na+], Reagents are:m3_m6:ClCCl;m1_m2_m5:ClCCl, and Products are 0:C1=CC=CC=2N(CCC=3N(C21)C=CC3)C(=O)C3=C(C=C(C=C3)NC(C3=C(C=C(C=C3)Cl)Cl)=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 0.10 g of 6,7-dihydro-5-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[1,2-a][1,5]benzodiazepine and 0.06 g of triethylamine in 6 ml of dichloromethane is added 0.10 g of 2,4-dichlorobenzoyl chloride in 0.5 ml of dichloromethane. The mixture is stirred at room temperature for 2 hours and 2 ml of 1N NaOH is added. The volatiles are removed under vacuum and to the residue is added 2 ml of tetrahydrofuran and 1 ml of methanol. The mixture is stirred at room temperature for 2 hours and the volatiles removed. To the residue is added 2 ml of 1N NaOH and 5 ml of H2O. The mixture is extracted with ethyl acetate and the extract washed with brine and dried (Na2SO4). The solvent is removed and the solid triturated with diethyl ether-hexane to give 0.15 g of white solid, Mass Spectrum (CI): 510(M+H, Cl35). |
Here is a chemical reaction formula: Reactants are:m1_m3:[Na].N1N=CN=C1;m2_m4:ClCC(=O)NC1=CC=C(C=C1)C(=O)N1CC=2N(CC3=C1C=CC=C3)C=CC2, Reagents are:m1_m3:CN1C(N(CCC1)C)=O;m2_m4:CN1C(N(CCC1)C)=O, and Products are 0:C=1C=CN2C1CN(C1=C(C2)C=CC=C1)C(=O)C1=CC=C(C=C1)NC(CN1N=CN=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 0.20 g of 1,2,4-triazole sodium in 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is added 0.10 g of 2-chloro-N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]acetamide in 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone followed by stirring at room temperature for 3 hours. The reaction mixture is quenched with 15 ml of water and the resulting solid is collected, washed with water and hexanes to give 70 mg of the desired product as a tan solid. MS(CI): 413 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m5_m2:ClC1=C(C=CC=C1)C(CC1=CC=C(C(=O)OC)C=C1)=O;m1_m4_m5_m2:[OH-].[Na+];m3:C(CC(O)(C(=O)O)CC(=O)O)(=O)O, Reagents are:m1_m4_m5_m2:CO;m1_m4_m5_m2:O, and Products are 0:ClC1=C(C=CC=C1)C(CC1=CC=C(C(=O)O)C=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 18.78 g of methyl 4-[2-(2-chlorophenyl)-2-oxoethyl]benzoate in 288.8 ml of CH3OH, 72.2 ml of water and 5.2 g of NaOH is refluxed for 3 hours then acidified with 2N citric acid. The reaction mixture is evaporated in vacuo to remove the CH3OH. The aqueous phase is extracted with CH2Cl2 and acidified with 1N HCl. The resulting solid is collected and dried under vacuum to give 17.27 g of the desired product, m.p. 168°-172° C. |
Here is a chemical reaction formula: Reactants are:m3:COC=1C=C(C(=O)Cl)C=CC1[N+](=O)[O-];m1_m4_m2:C=1C=CN2C1CNC1=C(C2)C=CC=C1;m1_m4_m2:C(C)N(CC)CC, Reagents are:m1_m4_m2:C(Cl)Cl, and Products are 0:[N+](=O)([O-])C1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0.55 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 8 ml of methylene chloride is added 0.55 g of triethylamine followed by 0.97 g of 3-methoxy-4-nitrobenzoyl chloride. The reaction mixture is stirred at room temperature for 2 hours and then quenched with 10 ml of 1N NaOH. The methylene chloride layer is evaporated and the resulting suspension filtered. The precipitate is washed with 1N NaOH (2×5 ml), water (3×5 ml) and hexane (2×5 ml). The collected solid is dried in vacuo to give 1.13 g of off-white solid. MS(CI): 364(M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:NC1=C(C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=C1)OC;m1_m4_m2:C(C)N(CC)CC;m3:C(CCC)S(=O)(=O)Cl, Reagents are:m1_m4_m2:C(Cl)Cl;m5:C(Cl)Cl, and Products are 0:COC=1C=C(C(=O)N2CC=3N(CC4=C2C=CC=C4)C=CC3)C=CC1NS(=O)(=O)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 0.10 g of 10,11-dihydro-10-(4-amino-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 2 ml of methylene chloride is added 60 mg of triethylamine followed by a solution of 56 mg of n-butylsulfonyl chloride in 0.5 ml of methylene chloride. After stirring at room temperature for 2 hours, the reaction mixture is evaporated in vacuo to a residue which is dissolved in methyl alcohol, stirred for 1 hour and evaporated in vacuo to a residue which is treated with 2 ml of NH4Cl and extracted with 15 ml of ethyl acetate. The organic extract is washed with saturated NaHCO3, brine, dried (Na2SO4), filtered through hydrous magnesium silicate and the filtrate evaporated to a residue. The residue is stirred with ether-hexanes to give 0.14 g of light yellow solid. MS(CI): 454 (M+H). |
Here is a chemical reaction formula: Reactants are:m0_m1_m2_m3:C1(CC(CCC1)=O)=O;m0_m1_m2_m3:CC(CO)(CO)C, Reagents are:m0_m1_m2_m3:C1(=CC=CC=C1)C, and Products are 0:CC1(COC2(OC1)CC(CCC2)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 125 g (630 mmole) 3,3-dimethyl-1,5-dioxa-spiro[5,5]undecan-8-one, which was obtained by the azeotropic acetylation of cyclohexane-1,3-dione with 2,2-dimethylpropane-1,3-diol in toluene as a solvent using p-toluenesulphonic acid as a catalyst, and 59 g (630 mmole) dimethylammonium methylene chloride were stirred at room temperature in 400 ml of dry acetonitrile. After adding 1 ml acetyl chloride the mixture was stirred for a further 3 hours at room temperature, whereupon a clear colourless solution was obtained. 800 ml of dry ether were then added drop-wise to the reaction mixture, whereupon the hydrochloride crystallised out. 158 g of (18) were obtained (98% theoretical). |
Here is a chemical reaction formula: Reactants are:m4_m5_m6_m10:CN(C)CC1C(CC(CC1)C(F)(F)F)=O;m4_m5_m6_m10:FC(C1CC(CCC1)=O)(F)F;m4_m5_m6_m10:CN(C)C(Cl)Cl;m1_m8:C(C1=CC=CC=C1)OC=1C=C(C=CC1)Br;m3:C(C1=CC=CC=C1)OC=1C=C(C=CC1)Br;m2_m9:[Mg];m7:[Cl-].[NH4+], Reagents are:m4_m5_m6_m10:C(C)#N;m11:O1CCCC1;m12:CCOCC;m1_m8:O1CCCC1;m2_m9:O1CCCC1, and Products are 0:C(C1=CC=CC=C1)OC=1C=C(C=CC1)C1(C(CCC(C1)C(F)(F)F)CN(C)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 43.9 g (167 mmole) 3-benzyloxy-1-bromobenzene, dissolved in 200 ml of dry tetrahydrofuran, were added drop-wise to 4.06 g (167 mmole) magnesium turnings in 40 ml of dry tetrahydrofuran so that the reaction mixture boiled gently. After the addition of 3-benzyloxy-1-bromobenzene was complete, the mixture was heated for one hour under reflux and was thereafter cooled to 5°-10° C. 30.8 g (139 mmole) (2RS,5SR)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone, prepared from 3-trifluoromethyl-cyclohexanone and dimethylaminomethylene chloride in acetonitrile, dissolved in 80 ml of dry tetrahydrofuran, were added at this temperature. The reaction mixture was allowed to stand overnight and was then cooled to 5°-10° C. again. The Grignard solution was decomposed by the addition of 150 ml of 20% ammonium chloride solution. The reaction mixture was diluted with 200 ml of ether, the organic phase was separated off and the aqueous phase was extracted twice with 100 ml ether. The combined organic phases were dried over sodium sulphate. After removing the solvent by distillation, the residue (60.6 g) was introduced on to an 8×50 cm column packed with silica gel and extracted with ethyl acetate/methanol. 27.8 g (50% theoretical) of base (26) were obtained. |
Here is a chemical reaction formula: Reactants are:m1:CN(C)CC1C(CC(CC1)C(F)(F)F)=O;m2_m3_m4:FC(C1CC(CCC1)=O)(F)F;m2_m3_m4:CN(C)C(Cl)Cl, Reagents are:m2_m3_m4:C(C)#N, and Products are 0:Cl.CN(C)CC1C(CC(CC1)C(F)(F)F)(O)C=1C=C(C=CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 5-epimer (27) of compound (25) was prepared, under the conditions given in Example 27, from (2RS,5RS)-2-dimethylaminomethyl-5-trifluoromethyl-cyclohexanone, prepared from 3-trifluoromethyl-cyclohexanone and dimethylaminomethylene chloride in acetonitrile. (27) was obtained in a yield of 27% theoretical and had a melting point of 221°-223° C. |
Here is a chemical reaction formula: Reactants are:m1_m7_m4_m2:C(C)(C)(C)N1N=C(NC1=O)C1=CC(=NC(=C1)Cl)Cl;m1_m7_m4_m2:C(=O)([O-])[O-].[K+].[K+];m3_m5:C(C#C)Br, Reagents are:m6:C(C)(=O)OCC;m1_m7_m4_m2:O;m1_m7_m4_m2:C(C)(=O)OCC;m3_m5:C1(=CC=CC=C1)C, and Products are 0:C(C)(C)(C)N1N=C(N(C1=O)CC#C)C1=CC(=NC(=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2.06 g (7.2 mmol) of crude 2-(t-butyl)-5-(2,6-dichloro-4-pyridyl)-1,2,4-triazolin-3-one were added 30 mL of ethyl acetate, 1 drop of water, and 1.00 g (7.30 mmol) of powdered K2CO3. The mixture was heated to reflux and after 15 min 1.10 g (7.4 mmol) of an 80% by weight solution of propargyl bromide in toluene was added. Refluxing was continued for 2.5 hours. The mixture was cooled, diluted with 175 mL of ethyl acetate, washed with 25 mL of water, and dried over MgSO4. Reomoval of the solvent left 2.18 g of crude product as a reddish solid. The crude product was combined with 0.69 g of material from another run and purified by flash chromatography first on a silica gel column and then on a neutral alumina column eluted portionwise in both cases with ether hexane mixtures containing successively greater percentages of ether to afford 0.97 g of 2-(t-butyl)-5-(2,6-dichloro-4-pyridyl)-4-propargyl-1,2,4-triazolin-3-one (Compound 1) as a white solid, m.p. 107°-109° C. 1H-NMR (CDCl3)∂1.6 (9H,s), 2.45 (1H,t), 4.6 (2H,d), 7.75 (2H,s). |
Here is a chemical reaction formula: Reactants are:m1_m3:C1(CC1)CN1C(=O)N(C=2N=CNC2C1=O)CC1CC1;m2:[N+](=O)(O)[O-], Reagents are:m1_m3:C(C)(=O)O, and Products are 0:C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CC1CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-cyclopropylmethyl xanthine (20 g, 0,076 mol) was dissolved in acetic acid (33 ml) and then treated with concentrated nitric acid (13.2 g) at 87° C. After 1 hour, the mixture was cooled to 5° C. and the resulting yellow precipitate filtered off. The yellow crystals were dissolved in dichloromethane and washed with water. The separated organic layer was then dried over anhydrous sodium sulphate and concentrated in vacuo. The product crystallized from the concentrate to yield a yellow crystalline product yield 12.2 g, (56.5%), m.pt. 207° C. (with decomposition). |
Here is a chemical reaction formula: Reactants are:m1_m2:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CCCC;m1_m2:Cl, Reagents are:, and Products are 0:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Cl)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-n-butyl-8-nitro xanthine (0.5 g, 0.0016 mol) was refluxed for 18 hours with concentrated hydrochloric acid (8 ml). The reaction mixture was extracted with dichloromethane (20 ml), the organic layer washed with water to neutrality and then dried over anhydrous sodium sulphate. The solvent was then removed by evaporation in vacuo and the residue was recrystallised from ethanol, to give the title compound, yield 0.38 g (73%), m.pt. 152° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CCCC;m1_m2:Br, Reagents are:, and Products are 0:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Br)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-n-butyl-8-bromo xanthine was prepared from 1,3-di-n-butyl-8-nitro xanthine (0.5 g, 0.0016 mol) and concentrated hydrobromic acid (8 ml) using the procedure as described in Example 15. The title product was obtained after recrystallisation from ethanol, yield 0.4 g (91%), m.pt. 178° C. |
Here is a chemical reaction formula: Reactants are:m0_m1_m2_m3:C1(CCCCC1)N1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])C1CCCCC1;m0_m1_m2_m3:P(=O)(Cl)(Cl)Cl, Reagents are:m0_m1_m2_m3:CN(C=O)C, and Products are 0:C1(CCCCC1)N1C(=O)N(C=2N=C(NC2C1=O)Cl)C1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-cyclohexyl-8-chloro xanthine was prepared from 1,3-di-cyclohexyl-8-nitro xanthine (2 g, 0.006 mol) and phosphorous oxychloride (3.9 g) in dimethylformamide (6 ml), using an analogous procedure to that described in Example 17. The product was obtained as a crystalline product after recrystallisation from ethyl acetate, m.pt., 135° C. |
Here is a chemical reaction formula: Reactants are:m2:N1CCCCC1;m1_m3:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Br)CCCC, Reagents are:m1_m3:C1(=CC=CC=C1)C, and Products are 0:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)N1CCCCC1)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-n-butyl-8-bromo xanthine (2 g, 0.0029 mol) was dissolved in toluene (50 ml). After addition of piperidine (5 g, 0.0058 mol) the mixture was refluxed for 9 hours. The reaction mixture was then extracted with water (4×30 ml), the organic layer dried over anhydrous sodium sulphate and the solvent removed in vacuo. The residue was recrystallised from ethanol to give the title product, yield 0.4 g (20%), m.pt. 221° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)Cl)CC1CC1;m1_m2:N1CCOCC1, Reagents are:, and Products are 0:C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)N1CCOCC1)CC1CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-cyclopropylmethyl-8-morpholino xanthine was prepared from 1,3-di-cyclopropylmethyl-8-chloroxanthine (0.3 g, 0.001 mol) and morpholine (0.2 g, 0.0022 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. >250° C., yield 0.09 g (26%). |
Here is a chemical reaction formula: Reactants are:m1_m2:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)Br)CCCC;m1_m2:N1CCCC1, Reagents are:, and Products are 0:C(CCC)N1C(=O)N(C=2N=C(NC2C1=O)N1CCCC1)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared from 1,3-di-n-butyl-8-bromo xanthine (1 g, 0.0029 ml) and pyrrolidine (0.041 g, 0.0057 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. >250° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)Cl)CC1CC1;m1_m2:N1CCCC1, Reagents are:, and Products are 0:C1(CC1)CN1C(=O)N(C=2N=C(NC2C1=O)N1CCCC1)CC1CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared from 1,3-di-cyclopropylmethyl-8-chloro xanthine (0.3 g, 0.0011 mol) and pyrrolidine (0.2 g, 0.0028 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. >250° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)Br)CC1CCCCC1;m1_m2:N1CCCCC1, Reagents are:, and Products are 0:C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)N1CCCCC1)CC1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared from 1,3-di-cyclohexylmethyl-8-bromo xanthine (0.7 g, 0.0017 mol) and piperidine (0.28 g, 0,003 mol) using an analogous procedure to that described in Example 19. The title product was obtained as a crystalline solid, m.pt. 266° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)[N+](=O)[O-])CC1CCCCC1;m1_m2:Br, Reagents are:, and Products are 0:C1(CCCCC1)CN1C(=O)N(C=2N=C(NC2C1=O)Br)CC1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared from 1,3-di-cyclohexylmethyl-8-nitro xanthine (1 g, 0.0026 mol) and concentrated hydrobromic acid (40 ml, 48%) over 32 hours using an analogous procedure to that described in Example 15. The title product was obtained as a crystalline solid, m.pt. 247° C. |
Here is a chemical reaction formula: Reactants are:m3:C(=O)O;m4:S(=O)([O-])S(=O)[O-].[Na+].[Na+];m2:N(=O)[O-].[Na+];m1_m5:C1(CC1)CN1C(=O)N(C(=O)C=C1N)CC1CC1;m1_m5:C(=O)N, Reagents are:, and Products are 0:C1(CC1)CN1C(=O)N(C=2N=CNC2C1=O)CC1CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-cyclopropylmethyl xanthine was prepared using an analogous procedure to that described in Chem. Berichte 88, 1306-1312, 1955: 20.2 g (0.0855 mol) of 1,3-dicyclopropylmethyl-6-amino-uracil was dissolved in 100 ml of formamide, then 5.9 g sodium nitrite was added and at 60° C. 13.4 ml formic acid was added slowly with stirring. After the colour had changed from yellow to violet, the mixture was heated up to 100° C. and 3.1 g of sodium dithionite (Na2S2O4) was added in small portions. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:NC(C(=O)N)C#N;m1_m2_m4:COC(OC)OC;m3:C(CC)N, Reagents are:m1_m2_m4:C(C)#N, and Products are 0:NC1=C(N=CN1CCC)C(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-amino-2-cyanoacetamide (2.8 g, 0.0282 mol), trimethylorthoformate (3.4 g, 0.0321 mol) and acetonitrile (55 ml) was heated under reflux for 0.75 hour, then allowed to cool. n-Propylamine (1.8 g, 0.0305 mol) was then added dropwise, and the resulting mixture stirred at ambient temperature for 36 hours. The solid which precipitated was collected by filtration and crystallised from methanol to give the title compound as a colourless solid (2.9 g, 61%), m.p. 241°-243° C. Found: C,49.67; H,7.15; N,33.64. C7 H12N4O requires C,49.98; H,7.19; N,33.31%. |
Here is a chemical reaction formula: Reactants are:m4_m6:NC1=C(N=CN1CCC)C(=O)N;m1_m2_m3_m5:C(C(=O)Cl)(=O)Cl;m1_m2_m3_m5:C(C)OC1=C(C(=O)O)C=CC=C1;m1_m2_m3_m5:CN(C=O)C, Reagents are:m4_m6:N1=CC=CC=C1;m1_m2_m3_m5:ClCCl, and Products are 0:C(C)OC1=C(C(=O)NC2=C(N=CN2CCC)C(=O)N)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Oxalyl chloride (1.74 g, 0.137 mol) was added dropwise to a stirred solution of 2-ethoxybenzoic acid (1.1 g, 0.00663 mol) and dimethylformamide (0.1 ml) in dichloromethane (20 ml) and the resulting mixture stirred at ambient temperature for 4 hours, then evaporated under vacuum. The residue was azeotroped with dichloromethane (2×20 ml), then added dropwise to a stirred solution of 5-amino-1-n-propylimidazole-4-carboxamide (0.9 g, 0.00536 mol) in pyridine (20 ml) The resulting solution was stirred at ambient temperature for 3 days, then evaporated under vacuum. The residue was dissolved in dichloromethane (50 ml), and the solution washed with 1N hydrochloric acid (30 ml), dried (Na2SO4) and evaporated under vacuum. Chromatography of the crude product on silica gel (15 g) using a methanol in dichloromethane elution gradient (2-6% methanol), followed by crystallisation from ethanol, gave the title compound as a colourless solid (1.3 g, 77%), m.p. 182°-184° C. Found: C,60.85; H,6.40; N,18.06. C16H20N4O3 requires C,60.74; H,6.37; N,17.71%. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1;m1_m4_m2_m3:N1C=NC=C1;m1_m4_m2_m3:C(C)(C)(C)[Si](C)(C)Cl, Reagents are:m1_m4_m2_m3:CN(C)C=O, and Products are 0:[Si](C)(C)(C(C)(C)C)OC[C@@H]1[C@H](C[C@@H](O1)N1C(=O)NC(=O)C(C)=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2.42 g (10 mmol) thymidine in 15 ml DMF was added 1.7 g (25 mmol) imidazole and 1.6 g (10.6 mmol) tert-butyldimethyl silyl chloride. The solution was stirred at room temperature for 3 hours. DMF was then removed in vacuo and the residue was dissolved in 150 ml of ethyl acetate. The solution was washed with water and the organic layer was dried over MgSO4. After removing the solvent, the solid was recrystallized with ethyl acetate/pentane to obtain 2.5 g pure 5'-O-(tert-butyldimethylsilyl) thymidine 1 (70% yield).: m.p. 193°-194° C.; 1H NMR (500 MHz, CDCl3) δ9.0 (s, 1H, NH), 7.50 (s, 1H, H-6), 6.36 (dd, J=5.8, 8.1 Hz, 1H, H-1'), 4.44 (m, 1H, H-3'), 4.03 (m, 1H, H-4'), 3.85 (m, 2H, H-5'), 2.66 (d, J=3.8 Hz, 1H, OH), 2.35 (m, 1H, H-2'), 2.07 (m, 1H, H-2'), 1.89 (s, 3H, C=CMe), 0.89 (s, 9H, CMe3), 0.09 (s, 6H, SiMe2); --NMR (125 MHz, CDCl3) δ163.8 (C-4), 150.4 (C-2), 135.4 (C-6), 110.9 (C-5), 87.2 (C-4'), 85.0 (C-1'), 72.6 (C-3'), 63.6 (C-5'), 41.1 (C-2'), 25.9 (SiCMe3), 18.3 (SiCMe3), 12.5 (C=CMe), -5.4 (SiMe2), -5.5 (SiMe2). |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m3:C(C)N(CC)CC;m1_m5_m2_m3:[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C(C)=C1;m1_m5_m2_m3:COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1;m4:CO, Reagents are:m1_m5_m2_m3:C1CCOC1, and Products are 0:COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(C)=C2)O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Triethylamine (10 ml) in 200 ml THF was injected into a solid mixture of 6.8 g (28.0 mmol) thymidine and 10.2 g (28.6 mmol) 4,4'-dimethoxytrityl chloride under nitrogen with stirring. The solution was stirred at room temperature for 2 hours. After completion of the reaction, 10 ml methanol was added to consume the excess DMTrCl. The mixture was stirred for 5 minutes and the solvent removed by rotary evaporation. The residue was dissolved in 250 ml of ethyl acetate and the solution was washed with saturated NaHCO3 and dried over MgSO4. The solid was recrystallized from ethyl acetate/hexane to obtain 13.0 g 5'-protected thymidine 16 (85.6%).: m.p. 124°-126° C.; 1H NMR (200 MHz, CDCl3) δ8.97 (s, 1H, NH), 7.60 (m, 1H, H-6), 6.72-7.42 (m, 13H, Ph), 6.42 (m, 1H, H-1'), 4.56 (m, 1H, H-3'), 4.05 (m, 1H, H-4'), 3.78 (s, 6H, OMe2), 3.41 (m, 2H, H-5'), 2.62 (m, 1H, OH), 2.46 (m, 2H, H-2'), 1.46 (s, 3H, Me); 13C NMR (50 MHz, CDCl3) δ163.0 (C-4), 157.6, 149.8 (C-2), 143.5, 135.0 (C-6), 134.7, 134.6, 129.4, 127.4, 127.3, 126.5, 112.8, 110.9 (C-5), 86.7 (C-4'), 86.2, 84.7 (C-1'), 72.5 (C-3'), 63.8 (C-5'), 55.5 (OCH3), 41.3 (C-2'), 12.5 (CH3). |
Here is a chemical reaction formula: Reactants are:m2:C(=O)([O-])[O-].[Na+].[Na+];m1_m3:COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@@H]2[C@H](C[C@@H](O2)N2C(=O)NC(=O)C(C)=C2)O[Si](C)(C)C(C)(C)C)C=C1, Reagents are:m1_m3:C(C)(=O)O, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C[C@@H](O[C@@H]1CO)N1C(=O)NC(=O)C(C)=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 5 g (7.6 mmol) 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl) thymidine 17 in 100 ml 80% aq. acetic acid was stirred until the removal of dimethoxytrityl group was completed. Saturated Na2CO3 was then added to adjust the pH of the solution to 6-7. The solution was then extracted with ethyl acetate. The extract was dried and the mixture was chromatographed on a silica gel column (CH2Cl2 :MeOH=20:1) to give 2.5 g of 3'-O-(tert-butyldimethylsilyl) thymidine 18 (92.6%).: m.p.93=20 -95° C. (lit. 83°-84° C.); H NMR (200 MHz CDCl3) δ9.18 (s, 1H, NH), 7.36 (b, 1H, H-6), 6.12 (t, J=6.8 Hz, 1H, H-1'), 4.44-4.48 (m, 1H, H-3'), 3.69-3.91 (m, 3H, H-4', H-5'), 2.87 (m, 1H, OH), 2.15-2.35 (m, 2H, H-2'), 1.87 (s, 3H, C=CMe), 0.86 (s, 9H, CMe3), 0.05 (s, 6H, SiMe2); 13C NMR (125 MHz, CDCl3) δ163.9 (C-4), 150.4 (C-2), 137.1 (C-6), 110.9 (C-5), 87.6 (C-4'), 86.8 (C-1'), 71.5 (C-3'), 61.9 (C-5'), 40.4 (C-2'), 25.7 (SiCMe3), 17.9 (SiCMe), 12.5 (C=CMe), -4.7 (SiMe2), -4.9 (SiMe2). |
Here is a chemical reaction formula: Reactants are:m3_m6:N(=O)[O-].[Na+];m1:C(CC)N1C(=O)N(C(=O)C=C1N)CCC;m2:C(C)(=O)O;m4:Cl, Reagents are:m3_m6:O;m5:O, and Products are 0:C(CC)N1C(=O)N(C(=O)C(=C1N)N=O)CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,3-Di-n-propyl-6-aminouracil (30 g) was suspended in 1 L of water with 41 ml of 20% acetic acid and overhead stirring. Sodium nitrite (9.03 g) in 41 ml of water was added in portions, keeping the solution acidic with 12 ml of concentrated hydrochloric acid. A purple precipitate formed. Addition was complete in 10 minutes and the suspension was allowed to stir for 2 hours. The solution was then filtered, and the filtrate was rinsed with water and dried under vacuum to yield 46 g of 1,3-di-n-propyl-5-nitroso-6-aminouracil. |
Here is a chemical reaction formula: Reactants are:m3:S(=O)([O-])S(=O)[O-].[Na+].[Na+];m2:[OH-].[NH4+];m1:C(CC)N1C(=O)N(C(=O)C(=C1N)N=O)CCC, Reagents are:m4:O, and Products are 0:C(CC)N1C(=O)N(C(=O)C(=C1N)N)CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 1,3-di-n-propyl-5-nitroso-6-aminouracil (61.6 g) was suspended in 1 L of water, and the suspension was made alkaline to pH 11 with 50% ammonium hydroxide and treated with 100 g of sodium dithionite, in portions, until the purple color faded. The aqueous mixture was extracted with chloroform (8×200 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (5/10% methanol/chloroform) and recrystallized from 10% isopropanol in hexane and recrystallized from 10% isopropanol to yield 37.29 g of 1,3-di-n-propyl-5,6-diaminouracil, m.p., 127°-128° C. |
Here is a chemical reaction formula: Reactants are:m4:C(CC)N1C(=O)N(C(=O)C(=C1N)N)CCC;m2:CN1CCOCC1;m1_m5:C1(=CC=CC=C1)C(CC(=O)O)C;m1_m5:O1CCCC1;m3:ClC(=O)OCC(C)C, Reagents are:m6:C(C)OCC, and Products are 0:NC1=C(C(C(C(C1CCC)=O)CCC)=O)NC(CC(C)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 3-phenylbutyric acid (1.0 g, 6.1 mmol) in tetrahydrofuran (20 ml), treat with N-methylmorpholine (0.67 ml, 6.1 mmol) and cool to -20° C. Add isobutyl chloroformate (0.79 ml, 6.1 mmol) and stir for 20 minutes. Then add 1,3-di-n-propyl-5,6-diaminouracil (1.4 g, 6.1 mmol, in 5 ml dimethylformamide) and stir the reaction at -20° C. for 3 hours. Then dilute the reaction with diethyl ether (400 ml) and separate the layers. Rinse the organic layer with saturated sodium bicarbonate (200 ml), 50% aqueous sodium chloride (2×200 ml), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum to provide N-(2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)-3-phenylbutyramide (2.23 g). |
Here is a chemical reaction formula: Reactants are:m4:C(CC)N1C(=O)N(C(=O)C(=C1N)N)CCC;m2:CN1CCOCC1;m3:ClC(=O)OCC(C)C;m1_m5:C1C(CCC2=CC=CC=C12)C(=O)O;m1_m5:O1CCCC1, Reagents are:m6:C(C)OCC, and Products are 0:NC1=C(C(C(C(C1CCC)=O)CCC)=O)NC(=O)C1CC2=CC=CC=C2CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve 1,2,3,4-tetrahydro-2-naphthoic acid (1.0 g, 5.67 mmol) in tetrahydrofuran (40 ml). Add N-methylmorpholine (0.62 ml, 5.67 mmol) and cool to -20° C. Add isobutyl chloroformate (0.73 ml, 5.67 mmol) and stir for 25 minutes. Then add 1,3-di-n-propyl-5,6-diaminouracil (1.28 g, 5.67 mmol, in 5 ml dimethylformamide) and stir the reaction for 5 hours at -20° C. Warm the reaction to room temperature and dilute with diethyl ether (300 ml). Separate the layers and rinse the organic layer with saturated sodium bicarbonate (200 ml), saturated sodium chloride solution (200 ml), dry over anhydrous magnesium sulfate, filter and concentrate. Purify the residue by radial chromatography (2% to 4% to 6% methanol/chloroform, 4 mm plate) to provide 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2-amino-4,6-dioxo-3,5-dipropylcyclohex-1-enyl)amide (2.0 g) as a foam. |
Here is a chemical reaction formula: Reactants are:m1:C(C=C)N1C(=O)N(C(=O)C(=C1N)N=O)CC=C;m2_m4:S(=O)([O-])S(=O)[O-].[Na+].[Na+], Reagents are:m3:C(C)(=O)OCC;m2_m4:O, and Products are 0:C(C=C)N1C(=O)N(C(=O)C(=C1N)N)CC=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 1,3-diallyl-5-nitroso-6-aminouracil (4.5 g) was suspended in 150 ml of ethyl acetate and treated with 23.6 g of sodium dithionite in 64 ml of water. After 1 hour, the layers were separated and the aqueous phase was extracted with ethyl acetate (4×100 ml). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated and the residue was purified by flash chromatography (10% methanol in chloroform) to yield 4.41 g of 1,3-diallyl-5,6-diaminouracil. |
Here is a chemical reaction formula: Reactants are:m4:ClC(=O)OCC(C)C;m5:C(C=C)N1C(=O)N(C(=O)C(=C1N)N)CC=C;m6_m3:CN1CCOCC1;m2:C1(=CC=CC=C1)[C@H]1[C@@H](CCC1)C(=O)O, Reagents are:m6_m3:O1CCCC1;m7:C(C)OCC, and Products are 0:C1(=CC=CC=C1)[C@H]1[C@@H](CCC1)C(=O)O;0:C(C=C)C1C(=C(C(C(C1=O)CC=C)=O)[NH-])N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve trans-2-phenyl-cyclopentanecarboxylic acid (1.0 g, 5.3 mmol), prepared according to F. G. Bordwell and J. Almy, J. Org. Chem., 38, 571 (1973), in tetrahydrofuran (20 ml) and add N-methylmorpholine (0.58 ml, 5.3 mmol). Cool the reaction to -20° C. and add isobutyl chloroformate (0.69 ml, 5.3 mmol). Stir the reaction for 30 minutes, add 1,3-diallyl-5,6-diaminouracil (1.2 g, 5.3 mmol, in 4 ml dimethylformamide) and stir at -20° C. for 3 hours. Warm to room temperature and dilute the reaction with diethyl ether (400 ml). Separate the layers and rinse the organic layer with saturated sodium bicarbonate (2×200 ml), 50% aqueous sodium chloride (2×300 ml), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by radial chromatography (2% to 5% methanol/chloroform, 2 mm plate) to provide trans-2-phenyl-cyclo-pentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enylamide (0.51 g). |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C=C)C1C(=C(C(C(C1=O)CC=C)=O)NC(=O)[C@H]1[C@@H](CCC1)C1=CC=CC=C1)N;m2:[OH-].[K+], Reagents are:m1_m3:C(C)O;m4:O, and Products are 0:C(C=C)C1C(C2=C(NC(=N2)C2C(CCC2)C2=CC=CC=C2)C(C1=O)CC=C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dissolve trans-2-phenylcyclopentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enyl)amide (300 mg, 0.76 mmol) in ethanol (100 ml), add 10% potassium hydroxide (100 ml) and heat the reaction to 60° C. for 4 hours. Cool the reaction and dilute with water (200 ml). Acidify with concentrated hydrochloric acid and extract with diethyl ether (400 ml). Rinse the organic extract with water (200 ml), saturated sodium chloride (200 ml), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by radial chromatography (40% to 50% ethyl acetate/hexane, 2 mm plate) to provide 5,7-diallyl-2-(2-phenylcyclopentyl)-1,7-dihydrobenzoimidazole-4,6-dione (149 mg). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:ClC1=C(C=C(C=C1)Cl)CC(=S)O;m1_m3_m2:S(=O)(Cl)Cl, Reagents are:m1_m3_m2:C(Cl)Cl, and Products are 0:ClC1=C(C=C(C=C1)Cl)CC(=S)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2,5-dichlorophenylthioacetic acid (13.0 g, 54.9 mmol) in methylene chloride (55 mL) and thionyl chloride (10 mL, 137 mmol) was heated at reflux for 3 h. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The residue was evaporated two times from toluene to give 14 g of 2,5-dichlorophenyl-thioacetyl chloride (100% yield) as a slightly colored product which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ4.13 (s, 2H), 7.22 (dd, J=2, 9 Hz, 1H), 7.35 (d, J=9 Hz, 1H), 7.39 (d, J=2 Hz, 1H). |
Here is a chemical reaction formula: Reactants are:m1_m4:[Cl-].OC(C[N+]1=CC=C(C=C1)SCC1=C(N2C([C@H]([C@H]2SC1)NC(CSC1=C(C=CC(=C1)Cl)Cl)=O)=O)C(=O)O)CNC(=O)OC(C)(C)C;m2:C1(=CC=CC=C1)OC;m3:FC(C(=O)O)(F)F, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:[Cl-].OC(C[N+]1=CC=C(C=C1)SCC1=C(N2C([C@H]([C@H]2SC1)NC(CSC1=C(C=CC(=C1)Cl)Cl)=O)=O)C(=O)O)CN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of 1-(2-hydroxy-3-t-butoxycarbonylamino-1-propyl)-4-[[(6R)trans-2-carboxy-8-oxo-7-[(2,5- dichlorophenylthio)acetamido]-5- thia-1-azabicyclo[4.2.0]-oct-2-en-3-yl]methylthio]pyridinium chloride (1.19 g, 1.58 mmol) in methylene chloride (22 mL) was cooled to 0° C. Anisole (3.4 mL) was added followed by trifluoroacetic acid (11 mL). The mixture was stirred for 30 min at 0° C. and 30 min at rt. The reaction mixture was concentrated in vacuo. The residue was stirred with ether until a yellow powder resulted. This solid was collected by filtration washing with ether. The crude product was stirred with ether (20 mL) for 45 min, and then the solid was collected by filtration. This was followed by similar treatments with acetone (1×10 mL) and then ether (1×20 mL). The final filtration gave 655 mg (54%) of the title compound as a yellow solid. 1H NMR (300 MHz, DMSO) δ2.80 (t, J=10, 1H), 3.06 (d, J=11, 1H), 3.31-3.44 (m, 1H), 3.60 (d, J=18, 1H), 3.90 (s, 2H), 4.10 (br s, 1H), 4.34-4.42 (m, 3H), 4.66 (d, J=12, 1H), 5.02 (d, J=5, 1H), 5.56 (t, J=6, 1H), 6.5-7.0 (br s, 1H), 7.21 (dd, J=2, 8, 1H), 7.41-7.46 (m, 2H), 8.12 (m, 2H), 8.30 (br s, 3H), 8.68 (m, 2H), 9.28 (m, 1H); MS (FIA) m/e 615 (MH+); Anal. calcd for C24H24 N4O5S3Cl2.HCl. HO2CCF3 : C, 40.71; H, 3.55; N, 7.30. Found: C, 40.70; H, 3.52; 7.38. |
Here is a chemical reaction formula: Reactants are:m5:O;m4:C(C(C)C)(=O)Cl;m3:C(C(C)C)(=O)Cl;m1_m6_m2:IC1=CC=C(N)C=C1;m1_m6_m2:N1=CC=CC=C1, Reagents are:m1_m6_m2:C(C)#N, and Products are 0:IC1=CC=C(C=C1)NC(C(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a dispersion of p-iodoaniline (219.0 g, 1 mol) in acetonitrile(1000 ml) was added pyridine (81.0 ml, 1 mol). Isobutyryl chloride (100.5 ml, 1 mol) was added dropwise to the mixture over 1 hour in an ice bath. The mixture was further stirred for one hour following the addition of isobutyryl chloride and to the mixture was added water (3000 ml). Precipitated crystalline solids were collected by filtration to give N-(4-iodophenyl)isobutyramide (281.7 g, Yield: 97%). |
Here is a chemical reaction formula: Reactants are:m2_m5:P(=O)(OC1=CC=CC=C1)(OC1=CC=CC=C1)Cl;m4_m7:C(C)(=O)O;m3_m6:C(C)N(CC)CC;m1_m8:ON1C(CCC1=O)=O, Reagents are:m2_m5:C(C)(=O)OCC;m4_m7:C(C)(=O)OCC;m3_m6:C(C)(=O)OCC;m1_m8:C(C)(=O)OCC, and Products are 0:C1(CCC(N1OC(C)=O)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.27 g (0.011 mol) of N-hydroxysuccinimide were initially introduced into 10 ml of ethyl acetate, a solution of 3.22 g (0.012 mol) of diphenyl chlorophosphate in 10 ml of ethyl acetate was added and then a solution of 2.53 g (0.025 mol) of triethylamine in 10 ml of ethyl acetate was added dropwise in the course of 10 minutes, the temperature rising to 41° C. A thick, white suspension resulted, which was treated with a solution of 0.6 g (0.01 mol) of acetic acid in 10 ml of ethyl acetate and heated at 45°-55° C. for 16 hours. After ending of the reaction, the solid was filtered off and washed with 2×3 ml of ethyl acetate. The combined filtrates were evaporated in vacuo and the semicrystalline residue which remained was washed by stirring with 20 ml of ethanol for 30 minutes. The white solid thus obtained was filtered off, washed with 2×3 ml of ethanol, sucked dry and then washed by stirring with 10 ml of isopropanol. After filtering off, washing with 2×2 ml of isopropanol and drying in vacuo, 1.1 g (70%) of white acetic acid succinimidyl ester were obtained. |
Here is a chemical reaction formula: Reactants are:m2:C([O-])([O-])=O.[K+].[K+];m3:C(=O)(OCC1=CC=CC=C1)Cl;m1_m4_m5:S1C(=CC=C1)CC(N)C(=O)O, Reagents are:m1_m4_m5:O;m1_m4_m5:O1CCOCC1;m6:O, and Products are 0:C(C1=CC=CC=C1)OC(=O)NC(CC=1SC=CC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 3.0 g (16.9 mmol) of β-thienyl-D,L-alanine in 75 mL of water and 60 mL of dioxane, was added 5.6 g (40.6 mmol) of anhydrous potassium carbonate, followed by 2.85 mL (20 mmol) of carbobenzyloxychloride. The resulting mixture was stirred rapidly for approximately one hour. When the reaction was substantially complete, as indicated by thin layer chromatography (21/7/7/9, EtOAc/AcOH/CH3 CN/H2O), the reaction mixture was concentrated. The resultant layers were separated and the aqueous layer was washed with 75 mL of diethyl ether and then layered with 150 mL of methylene chloride. The resultant mixture was acidified with rapid stirring to pH=2.0 using 5N hydrochloric acid. The layers were then separated, and the organic layer was dried with sodium sulfate (Na2SO4), filtered and concentrated to provide 5.05 g of desired compound (98%). |
Here is a chemical reaction formula: Reactants are:m2:C(CC=O)CC=O;m1:C1(C=2C(C(N1N[C@@H](CC1=CC=CC=C1)C(=O)N)=O)=CC=CC2)=O;m5_m0:O1CCCC1.ClCCl;m3:O;m4:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m6:ClCCl, and Products are 0:O=C1N(C(C2=CC=CC=C12)=O)[C@H](C(=O)N1C=CCC=C1)CC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Combine phthalimido-(S)-phenyalanine amide (3.0 g, 10 mmol) and a solution of glutaric dialdehyde (2.0 g; 50% by weight in water) in dichloromethane (200 mL). Heat to reflux with azeotropic removal of water from the refluxate. Add p-toluenesulfonic acid (60 mg). Continue heating at reflux. Pass the refluxate through oven dried 4 Å molecular sieves. After 4 days, cool the reaction mixture to ambient temperature. Extract with 5% sodium bicarbonate solution. Extract the 5% sodium bicarbonate solution with dichloromethane. Combine the organic layers and dry over Na2 SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% tetrahydrofuran/dichloromethane to give the title compound. |