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Here is a chemical reaction formula: Reactants are:m2:C(#N)C1=CC=C(C(=O)O)C=C1;m1:COC1=CC=C(C=C1)N, Reagents are:, and Products are 0:C(#N)C1=CC=C(C(=O)NC2=CC=C(C=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using p-anisidine (1.35 g, 11.0 mmol) and 4-cyanobenzoic acid (1.47 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.31 g (91.7%) of the title compound in the form of colorless needle crystals. |
Here is a chemical reaction formula: Reactants are:m2:CC=1C=C(C(=O)O)C=CC1[N+](=O)[O-];m1:COC1=CC=C(C=C1)N, Reagents are:, and Products are 0:CC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using p-anisidine (738 mg, 6.0 mmol) and 3-methyl-4-nitrobenzoic acid (906 mg, 5.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.33 g (93.0%) of the title compound in the form of yellow powder. |
Here is a chemical reaction formula: Reactants are:m2:COC=1C=C(C(=O)O)C=CC1[N+](=O)[O-];m1:COC1=CC=C(C=C1)N, Reagents are:, and Products are 0:COC=1C=C(C(=O)NC2=CC=C(C=C2)OC)C=CC1[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using p-anisidine (738 mg, 6.0 mmol) and 3-methoxy-4-nitrobenzoic acid (986 mg, 5.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.40 g (92.7%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1;m1:NC1=CC=C(C=C1)C, Reagents are:, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using p-toluidine (1.19 g, 11.0 mmol) and 4-nitrobenzoic acid (1.77 g, 10.5 mmol), the procedure of Reference Example 16 was repeated to obtain 2.68 g (99.6%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are:m1:FC1=CC=C(N)C=C1;m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, Reagents are:, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)F)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-fluoroaniline (1.0 ml, 9.93 mmol) and 4-nitrobenzoic acid (1.58 g, 9.36 mmol), the procedure of Reference Example 16 was repeated to obtain 1.60 g (65.8%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1;m1:NC1=CC=CC=C1, Reagents are:, and Products are 0:[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=CC=C2)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using aniline (1.50 ml, 16.5 mmol) and 3-nitrobenzoic acid (2.64 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.84 g (78.2%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C=C1)C;m2:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1, Reagents are:, and Products are 0:[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)C)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using p-toluidine (1.19 g, 11.0 mmol) and 3-nitrobenzoic acid (1.76 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.27 g (88.3%) of the title compound in the form of colorless needle crystals. |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1;m1:FC1=CC=C(N)C=C1, Reagents are:, and Products are 0:[N+](=O)([O-])C=1C=C(C(=O)NC2=CC=C(C=C2)F)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-fluoroaniline (1.1 ml, 10.9 mmol) and 3-nitrobenzoic acid (1.76 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 1.98 g (76.0%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1;m1:CSC=1C=C(N)C=CC1, Reagents are:, and Products are 0:[N+](=O)([O-])C=1C=C(C(=O)NC2=CC(=CC=C2)SC)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3-methylthioaniline (2.1 ml, 16.5 mmol) and 3-nitrobenzoic acid (2.64 g, 15.0 mmol), the procedure of Reference Example 16 was repeated to obtain 4.09 g (94.6%) of the title compound in the form of light yellow needle crystals. |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1;m1:NC1=CC(=C(C=C1)C)C, Reagents are:, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=C(C=C2)C)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3,4-xylidine (1.35 g, 11.0 mmol) and 4-nitrobenzoic acid (1.69 g, 10.0 mmol), the procedure of Reference Example 16 was repeated to obtain 2.70 g (quantitative) of the title compound in the form of light yellow crystals. |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1;m1:NC1=CC(=CC(=C1)C)C, Reagents are:, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC(=CC(=C2)C)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3,5-xylidine (1.42 ml, 11.0 mmol) and 4-nitrobenzoic acid (1.76 g, 10.4 mmol), the procedure of Reference Example 16 was repeated to obtain 2.72 g (quantitative) of the title compound in the form of light yellow crystals. |
Here is a chemical reaction formula: Reactants are:m1:ClC1=CC=C(N)C=C1;m2:[N+](=O)([O-])C1=CC=C(C(=O)O)C=C1, Reagents are:, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC=C(C=C2)Cl)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-chloroaniline (1.42 g, 11.0 mmol) and 4-nitrobenzoic acid (1.76 g, 10.4 mmol), the procedure of Reference Example 16 was repeated to obtain 2.84 g (98.5%) of the title compound in the form of yellow crystals. |
Here is a chemical reaction formula: Reactants are:m1:C1OC=2C=C(N)C=CC2O1;m2:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1, Reagents are:, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)NC2=CC3=C(C=C2)OCO3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3,4-methylenedioxyaniline (1.44 g, 10.5 mmol) and 4-nitrobenzoyl chloride (1.86 g, 10.0 mmol), the procedure of Reference Example 11 was repeated to obtain 2.49 g (87.2%) of the title compound in the form of yellow crystals. |
Here is a chemical reaction formula: Reactants are:m2_m3:C(C)N(CC)CC;m2_m3:ClC(=O)OCC;m1_m6:COC1=C(NS(=O)(=O)C2=CC=C(C(=O)O)C=C2)C=CC=C1;m5:Cl;m4_m7:[BH4-].[Na+], Reagents are:m1_m6:C1CCOC1;m4_m7:O, and Products are 0:OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon and with cooling in an ice bath, 4-[(2-methoxyanilino)sulfonyl]benzoic acid (150 mg, 0.488 mmol) was dissolved in THF (5 ml), to which were subsequently added dropwise triethylamine (0.14 ml, 1.0 mmol) and ethyl chloroformate (50 μl, 0.509 mmol). After 30 minutes of stirring at the same temperature, the thus formed precipitate was removed by filtration, and the resulting filtrate was concentrated. The thus obtained residue was dissolved in 5 ml of THF, and, with cooling in an ice bath, sodium borohydride (46.5 mg, 1.22 mmol) and water (1 ml) were added to the resulting solution. After 40 minutes of stirring at the same temperature, the reaction mixture was adjusted to pH 4 to 5 with 2N hydrochloric acid and extracted with ether. The organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate. After removing the solvent by evaporation, the resulting colorless oily material was purified by silica gel column chromatography (ether) to obtain 99.6 mg (69.6%) of the title compound in the form of colorless solid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1;m1_m3_m4:CO.C1CCOC1;m2:[OH-].[Na+], Reagents are:, and Products are 0:COCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Chloromethyl-N-(2-methoxyphenyl)benzamide (138 mg, 0.50 mmol) was dissolved in a methanol-THF (1:1) mixture solution (6 ml) to which was subsequently added 10% sodium hydroxide aqueous solution (3 ml) at room temperature. After 14 hours of stirring at the same temperature, the reaction solution was subjected to 3 hours of ultrasonic treatment. After removing the organic solvent by evaporation, the resulting residue was extracted with methylene chloride and dried on anhydrous magnesium sulfate. After removing the solvent by evaporation, the resulting colorless oily material was purified by silica gel column chromatography (ether:hexane=1:2) to obtain 126 mg (92.9%) of the title compound in the form of colorless oil. |
Here is a chemical reaction formula: Reactants are:m2:O1CCCC=C1;m3:O.C1(=CC=C(C=C1)S(=O)(=O)O)C;m1_m5:OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC;m4:C([O-])(O)=O.[Na+], Reagents are:m1_m5:C(Cl)Cl, and Products are 0:O1C(CCCC1)OCC1=CC=C(C=C1)S(=O)(=O)NC1=C(C=CC=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide (99.6 mg, 0.34 mmol) was dissolved in methylene chloride (3 ml) to which, with cooling in an ice bath, were subsequently added 3,4-dihydro-2H-pyrane (48 μl, 0.51 mmol) and a catalytically effective amount of p-toluenesulfonic acid monohydrate. After 90 minutes of stirring at the same temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution (5 ml) and extracted with ether. The resulting organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate, and the solvent was removed by evaporation. Thereafter, the thus obtained light yellow oily material was purified by a silica gel column chromatography (ether:hexane=1:1) to obtain 117 mg (91.2%) of the title compound in the form of colorless solid. |
Here is a chemical reaction formula: Reactants are:m1_m5:C1(C=2C(C(N1)=O)=CC=CC2)=O;m4:[I-].[Na+];m3:ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1;m2:[H-].[Na+], Reagents are:m1_m5:C1CCOC1;m6:CN(C)C=O, and Products are 0:COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, phthalimide (150 mg, 1.0 mmol) was dissolved in THF (10 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After 40 minutes of stirring at the same temperature, to this was added a DMF solution (5 ml) containing 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) and a catalytically effective amount of sodium iodide. After 2 hours of stirring at 80° C. and subsequent removal of the solvent by evaporation, the resulting residue was mixed with water (10 ml) and extracted with an ethyl acetate-methylene chloride (1:2) mixture solution. The resulting organic layer was washed with water and saturated brine and dried on anhydrous magnesium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was subjected to a silica gel column chromatography (methylene chloride-ether:hexane=2:1) and then washed with ether to obtain 300 mg (77.6%) of the title compound in the form of colorless solid. |
Here is a chemical reaction formula: Reactants are:m2:C(CCC)[Li];m3:ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1;m4:C1CCOC1;m1_m5:N1CCOCC1, Reagents are:m6:O;m1_m5:CCOCC, and Products are 0:COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN1CCOCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, morpholine (192 mg, 2.2 mmol) was dissolved in ether (5 ml) to which, with cooling in an ice bath, was subsequently added n-butyl lithium (1.45 ml, 1.52M, 2.2 mmol). After 5 minutes of stirring at room temperature, to this was added 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) at the same temperature. After adding THF (5 ml) and stirring for 2.5 hours at 60° C., the reaction solution was mixed with water (20 ml) and extracted with ethyl acetate. After removing insoluble materials by filtration, the organic layer was washed with water and saturated brine and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether) to obtain 128 mg (39.2%) of the title compound in the form of light yellow solid. |
Here is a chemical reaction formula: Reactants are:m1:ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1;m2:CNC, Reagents are:m3:O1CCOCC1, and Products are 0:COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CN(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) was put into a 25 ml capacity eggplant type flask equipped with a cold finger and dissolved in dioxane (3 ml), followed by the addition of 50% dimethylamine aqueous solution (3 ml) at room temperature. After 2.5 hours of stirring at 80° C. and subsequent removal of dioxane by evaporation, the resulting residue was diluted with ethyl acetate (30 ml). The thus diluted solution was dried on anhydrous sodium carbonate, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether-ethyl acetate-ethyl acetate:methanol=10:1) to obtain 284 mg (100%) of the title compound in the form of colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m3:ClCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1;m2:CN, Reagents are:m1_m3:O1CCOCC1;m4:O1CCOCC1, and Products are 0:COC1=C(C=CC=C1)NC(C1=CC=C(C=C1)CNC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Chloromethyl-N-(2-methoxyphenyl)benzamide (400 mg, 1.45 mmol) was dissolved in dioxane (4 ml) and then mixed with 50% methylamine aqueous solution (4 ml) at room temperature. After 1 hour of stirring at the same temperature, dioxane was removed by evaporation, and the resulting residue was diluted with methylene chloride (10 ml). After drying on anhydrous sodium carbonate, the solvent was removed by evaporation to obtain 500 mg (100%) of the title compound in the form of colorless oil. |
Here is a chemical reaction formula: Reactants are:m3:BrCC1OCCO1;m1:COC=1C(=CC=CC1)N;m4_m5:[OH-].[Na+];m4_m5:ClCC1=CC=C(C(=O)Cl)C=C1;m2:C(C)N(CC)CC, Reagents are:m6:C(Cl)Cl, and Products are 0:ClCC1=CC=C(C(=O)N(CC2OCCO2)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, a mixture consisting of o-anisidine (500 mg, 4.06 mmol), triethylamine (1.6 ml, 11.5 mmol) and 2-bromomethyl-1,3-dioxolan (0.96 ml, 8.18 mmol) was stirred at 80° C. for 4 days, dissolved in methylene chloride (8 ml) and then, with cooling in an ice bath, mixed with 20% sodium hydroxide aqueous solution (4 ml) and 4-chloromethylbenzoyl chloride (768 mg, 4.06 mmol). After 1 hour of stirring at the same temperature, the resulting mixture was extracted with methylene chloride, washed with 10% citric acid aqueous solution and saturated brine and then dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ethyl acetate:hexane=2:5) to obtain 704 mg (47.9%) of the title compound in the form of colorless solid. |
Here is a chemical reaction formula: Reactants are:m1_m3:FC1=CC=C(C(=O)C2CCNCC2)C=C1;m2:BrCCO, Reagents are:m1_m3:C(C)N(CC)CC, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCO)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, 4-(4-fluorobenzoyl)piperidine (2.07 g, 10 mmol) was dissolved in triethylamine (30 ml) to which was subsequently added dropwise 2-bromoethanol (1.1 ml, 14.7 mmol) at room temperature. After 1 hour of heating under reflux, triethylamine was removed by evaporation, and the resulting residue was mixed with saturated sodium carbonate aqueous solution (40 ml) and extracted with ethyl acetate. The resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ethyl acetate-methylene chloride:methanol=10:1) to obtain 1.96 g (78.0%) of the title compound in the form of light yellow solid. |
Here is a chemical reaction formula: Reactants are:m2_m3:CN(C)C=O;m2_m3:S(=O)(Cl)Cl;m1_m4:FC1=CC=C(C(=O)C2CCN(CC2)CCO)C=C1, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:Cl.ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of dry air, 4-(4-fluorobenzoyl)-1-(2-hydroxyethyl)piperidine (1.96 g, 7.8 mmol) was dissolved in methylene chloride (10 ml) to which, with cooling in an ice bath, were subsequently added dropwise DMF (0.1 ml) and thionyl chloride (2.5 ml, 34.2 mmol). After 7 hours of stirring at room temperature, the solvent was removed by evaporation, and the resulting residue was subjected to azeotropic distillation using benzene (15 ml×2). Thereafter, the thus obtained residue was washed with an ether-methylene chloride (4:1) mixture solution (30 ml) to obtain 2.3 g (96.3%) of the title compound in the form of light beige powder. |
Here is a chemical reaction formula: Reactants are:m2:C([O-])([O-])=O.[Na+].[Na+];m1:Cl.ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O, Reagents are:m3:CCOCC, and Products are 0:ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-(2-Chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride (800 mg, 2.61 mmol) was suspended in ether (20 ml). With cooling in an ice bath, saturated sodium carbonate aqueous solution (5 ml) was added dropwise to the suspension. The reaction solution was extracted with ether and washed with saturated brine, and the resulting organic layer was dried on anhydrous sodium carbonate. Thereafter, the organic layer was filtered through silica gel (5 g), the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ether) to obtain 650 mg (92.3%) of the title compound in the form of light yellow solid. |
Here is a chemical reaction formula: Reactants are:m3:C(C)N(CC)CC;m1_m4:FC1=CC=C(C(=O)C2CCNCC2)C=C1;m2:C(C)OC(CBr)OCC, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:C(C)OC(CN1CCC(CC1)C(C1=CC=C(C=C1)F)=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-(4-Fluorobenzoyl)piperidine (207 mg, 1.0 mmol) was dissolved in methylene chloride (5 ml) to which were subsequently added bromoacetoaldehyde diethylacetal (305 mg, 1.5 mmol) and triethylamine (0.5 ml). After 12 hours of heating under reflux, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether) to obtain 81 mg (25.0%) of the title compound in the form of orange oil. |
Here is a chemical reaction formula: Reactants are:m5:C([O-])([O-])=O.[Na+].[Na+];m4:C(#N)[BH3-].[Na+];m2:Cl;m1_m6:C(C)OC(CN1CCC(CC1)C(C1=CC=C(C=C1)F)=O)OCC;m3:COC=1C(=CC=CC1)N, Reagents are:m1_m6:C1CCOC1;m7:CO, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCNC2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-(2,2-Diethoxyethyl)-4-(4-fluorobenzoyl)piperidine (81 mg, 0.25 mmol) was dissolved in THF (3 ml) to which was subsequently added 10% hydrochloric acid (2 ml) at room temperature. After 1 hour of stirring at the same temperature, the solvent was removed by evaporation, and the resulting residue was subjected to azeotropic distillation using benzene (5 ml×4) to obtain an orange glutinous material. The thus obtained residue was dissolved in methanol (2 ml) to which were subsequently added o-anisidine (29 μl, 0.25 mmol) and sodium cyanoborohydride (11 mg, 0.166 mmol) at room temperature. After 2 hours of stirring at the same temperature, the reaction solution was mixed with saturated sodium carbonate aqueous solution (10 ml), extracted with ethyl acetate and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation and then the resulting residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=2:1-ether) to obtain 59 mg (66.2%) of the title compound in the form of colorless solid. |
Here is a chemical reaction formula: Reactants are:m3:O1C(CCCC1)OCCBr;m1_m4:COC=1C=C(C(=O)NC2=C(C=CC=C2)OC)C=CC1;m2:[H-].[Na+], Reagents are:m1_m4:CN(C)C=O, and Products are 0:O1C(CCCC1)OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, 3-methoxy-N-(2-methoxyphenyl) benzamide (500 mg, 1.94 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (85 mg, 60%, 2.13 mmol) at room temperature, followed by 20 minutes of stirring. After additional 5 minutes of stirring under an ultrasonic irradiation condition at the same temperature, to this was added 2-tetrahydropyranyloxyethyl bromide (446 mg, 2.13 mmol) at room temperature. After 1 hour of stirring at room temperature and subsequent stirring at 70° C. for 6 hours, DMF was removed by evaporation, and the resulting residue was mixed with water (20 ml), extracted with ether and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting orange oily residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=2:1) to obtain 501 mg (67.0%) of the title compound in the form of yellow oil. |
Here is a chemical reaction formula: Reactants are:m2:O.C1(=CC=C(C=C1)S(=O)(=O)O)C;m3:C([O-])(O)=O.[Na+];m1_m4:COC=1C=C(C(=O)N(CCOC2OCCCC2)C2=C(C=CC=C2)OC)C=CC1, Reagents are:m1_m4:CO, and Products are 0:OCCN(C(C1=CC(=CC=C1)OC)=O)C1=C(C=CC=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide (501 mg, 1.30 mmol) was dissolved in methanol (4 ml) to which was subsequently added a catalytically effective amount of p-toluenesulfonic acid monohydrate and stirred for 3 hours at room temperature. The reaction solution was mixed with saturated sodium bicarbonate aqueous solution (10 ml) and extracted with ether, and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting colorless oily residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=3:1) to obtain 340 mg (86.8%) of the title compound in the form of light yellow oil. |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1_m3:COC1=C(C=CC=C1)N(C(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O)CC2OCCO2, Reagents are:m1_m3:C1CCOC1, and Products are 0:C(=O)CN(C(C1=CC=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)=O)C2=C(C=CC=C2)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-(2-Methoxyphenyl)-N-(1,3-dioxolan-2-yl)methyl-4-phthalimidomethylbenzamide (450 mg, 0.953 mmol) was dissolved in THF (6 ml) to which was subsequently added 10% hydrochloric acid (4 ml) at room temperature. After 2 hours of stirring at 60° C., the resulting reaction solution was extracted with chloroform and washed with saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting residue was mixed with 5 ml of chloroform to remove insoluble materials by filtration, thereby obtaining 300 mg (73.5%) of the title compound in the form of yellow oil which was used in the subsequent reaction without further purification. |
Here is a chemical reaction formula: Reactants are:m4:[H-].[Na+];m1_m2_m3_m5:COCC1=CC=C(C(=O)NC2=C(C=CC=C2)OC)C=C1;m1_m2_m3_m5:Cl.ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O;m1_m2_m3_m5:[I-].[Na+], Reagents are:m1_m2_m3_m5:CN(C)C=O, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)COC)=O)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, 4-methoxymethyl-N-(2-methoxyphenyl)benzamide (126 mg, 0.464 mmol), 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine hydrochloride (157 mg, 0.511 mmol) and sodium iodide (154 mg, 1.02 mmol) were dissolved in DMF (3 ml) to which was subsequently added sodium hydride (40 mg, 60%, 1.0 mmol) at room temperature. After stirring at room temperature for 10 minutes and then at 60° C. for 3.5 hours, DMF was removed by evaporation. The resulting residue was diluted with water (10 ml) and extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by subjecting it to a silica gel column chromatography (methylene chloride:methanol=80:1-ethyl acetate) to obtain 128 mg (54.7%) of the title compound in the form of colorless oil. |
Here is a chemical reaction formula: Reactants are:m4:ClCCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O;m1_m2_m5:COC1=C(C=CC=C1)NS(=O)(=O)C1=CC=C(C=C1)C;m1_m2_m5:[I-].[Na+];m3:[H-].[Na+], Reagents are:m7:CN(C)C=O;m6:CN(C)C=O;m1_m2_m5:CN(C)C=O, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, N-(2-methoxyphenyl)-p-toluenesulfonamide (277 mg, 1.0 mmol) and a catalytically effective amount of sodium iodide were dissolved in DMF (3 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After stirring at the same temperature for 30 minutes and then at 60° C. for 10 minutes, 1-(2-chloroethyl)-4-(4-fluorobenzoyl)piperidine (324 mg, 1.2 mmol) which has been divided into 3 portions, each being dissolved in DMF (1 ml), was added to the reaction solution at 1 hour intervals at 60° C. After 1.5 hours of additional stirring at the same temperature, DMF was removed by evaporation. The thus obtained residue was diluted with water (10 ml) and extracted with ether. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (ether:hexane=2:1) to obtain 467 mg (91.5%) of the title compound in the form of colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m4:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)COC2OCCCC2)C2=C(C=CC=C2)OC)C=C1;m3:C([O-])(O)=O.[Na+];m2:O.C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m1_m4:CO;m5:CO, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CO)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-tetrahydropyranyloxymethyl-N-(2-methoxyphenyl)benzene sulfonamide (101 mg, 0.165 mmol) was dissolved in methanol (5 ml) to which was subsequently added p-toluenesulfonic acid monohydrate (35 mg, 0.18 mmol) at room temperature. After 2 hour of stirring at the same temperature, methanol was removed by evaporation, and the resulting reaction solution was mixed with saturated sodium bicarbonate aqueous solution (5 ml), extracted with ethyl acetate, and washed with water and saturated brine. The water layer was extracted with ethyl acetate, and washed with water and saturated brine, and the organic layers were combined and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate) to obtain 87 mg (100%) of the title compound in the form of colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m3:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CO)C2=C(C=CC=C2)OC)C=C1, Reagents are:m2:C(Cl)Cl;m1_m3:C(Cl)Cl;m4:[O-2].[O-2].[Mn+4], and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C=O)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Activated manganese dioxide (870 mg, 10.0 mmol) was suspended in methylene chloride (10 ml), and N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzene sulfonamide (259 mg, 0.492 mmol) dissolved in methylene chloride (3 ml) was added to the suspension. After 30 minutes of stirring at room temperature, the reaction mixture was filtered through silica gel (1 g) which was further subjected to elution with ethyl acetate. Thereafter, the filtrate and eluate were combined, and the solvent was removed by evaporation to obtain 211 mg (81.7%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m2_m5:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)C=O)C2=C(C=CC=C2)OC)C=C1;m1_m2_m5:Cl.ON;m3:C([O-])([O-])=O.[Na+].[Na+], Reagents are:m1_m2_m5:C(C)O, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-4-formyl-N-(2-methoxyphenyl)benzenesulfonamide (63 mg, 0.12 mmol) and hydroxyamine hydrochloride (9.5 mg, 0.132 mmol) were dissolved in ethanol (2 ml) to which were subsequently added anhydrous sodium carbonate (14 mg, 0.132 mmol) and water (1 ml). After 1.5 hours of stirring at room temperature, ethanol was removed by evaporation, and the resulting residue was mixed with water (10 ml) to collect crystals by filtration. The thus collected crystals were washed with water and hexane, dissolved in methylene chloride (50 ml) and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation to obtain 65 mg (100%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are:m4:N(=NC(=O)OCC)C(=O)OCC;m1_m2_m3_m5:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CO)=O)C2=C(C=CC=C2)OC)C=C1;m1_m2_m3_m5:C1(CCC(N1)=O)=O;m1_m2_m3_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m6:O;m1_m2_m3_m5:C1CCOC1, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CN2C(CCC2=O)=O)=O)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-hydroxymethyl-N-(2-methoxyphenyl)benzamide (54 mg, 0.11 mmol), succinimide (13 mg, 0.132 mmol) and triphenylphosphine (34.6 mg, 0.132 mmol) were dissolved in THF (1 ml) to which was subsequently added dropwise diethyl azodicarboxylate (21 μl, 0.132 mmol) while cooling in an ice bath. After 30 minutes of stirring at room temperature, the reaction solution was diluted with water (10 ml) and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a PTLC (chloroform:methanol=20:1) to obtain 42 mg (66.8%) of the title compound in a light yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m1_m4_m5:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CC=C(C=C2)CN2C(C=3C(C2=O)=CC=CC3)=O)C3=C(C=CC=C3)OC)C=C1;m3:C([O-])(O)=O.[Na+];m2:O.NN, Reagents are:m6:C(C)(=O)OCC;m1_m4_m5:CO.C1CCOC1, and Products are 0:NCC1=CC=C(C=C1)S(=O)(=O)N(C1=C(C=CC=C1)OC)CCN1CCC(CC1)C(C1=CC=C(C=C1)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)-4-phthalimidomethylbenzenesulfonamide (77 mg, 0.117 mmol) was dissolved in a methanol-THF (3:2) mixture solution (2.5 ml) to which was subsequently added hydrazine hydrate (1 ml) while cooling in an ice bath. After 15 minutes of stirring at the same temperature, the organic solvent was removed by evaporation, and the resulting residue was extracted with methylene chloride. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dried on anhydrous sodium carbonate, followed by the removal of the solvent by evaporation. To the resulting residue was added an acetic acid-THF-water (3:1:1) mixture solution (3 ml). After 2 hours of stirring at room temperature, the solvent was removed by evaporation, and the resulting reaction solution was diluted with ethyl acetate (15 ml), mixed with saturated sodium bicarbonate aqueous solution (5 ml) and then extracted with ethyl acetate. After drying the extract on anhydrous sodium carbonate, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (methylene chloride:methanol=20:1 to 9:1) to obtain 47 mg (76.4%) of the title compound in a colorless oily form. |
Here is a chemical reaction formula: Reactants are:m2_m3:Cl;m2_m3:[Sn];m1_m5:[N+](=O)([O-])C1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m4:[OH-].[Na+], Reagents are:m1_m5:CO;m7:C(Cl)(Cl)Cl, and Products are 0:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Nitro-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (264.0 mg, 0.52 mmol) was dissolved in methanol (5 ml) to which were subsequently added concentrated hydrochloric acid (2.0 ml) and tin (powder, 186.0 mg, 1.57 mmol) while cooling in an ice bath. After 1 hour of stirring at room temperature, the reaction solution was poured in ice water, adjusted to pH 9 to 10 with 10% sodium hydroxide aqueous solution, mixed with chloroform and then passed through cerite to remove insoluble materials. The resulting residue was washed with chloroform, the filtrate was extracted with chloroform, and the resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) to obtain 243.0 mg (97.9%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (2.65 g, 5.58 mmol) and acetic anhydride (0.79 ml, 8.37 mmol), the procedure of Inventive Example 94 was repeated to obtain 2.44 g (84.3%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (1.00 g, 2.10 mmol) and acetic anhydride (0.24 ml, 2.54 mmol), the procedure of Inventive Example 94 was repeated to obtain 851.0 mg (78.3%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (556.9 mg, 1.17 mmol) and acetic anhydride (0.13 ml, 1.41 mmol), the procedure of Inventive Example 94 was repeated to obtain 476.8 mg (78.7%) of the title compound in the form of colorless powder. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=CC=C(C(=O)N(C2=C(C=CC(=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC(=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2,5-dimethoxyphenyl)benzamide (170.0 mg, 0.34 mmol) and acetic anhydride (0.16 ml, 1.70 mmol), the procedure of Inventive Example 94 was repeated to obtain 132.0 mg (71.5%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1, Reagents are:, and Products are 0:C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (216.0 mg, 0.45 mmol) and acetic anhydride (0.051 ml, 0.54 mmol), the procedure of Inventive Example 97 was repeated to obtain 197.5 mg (84.9%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=C(C=C(C=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=C(C=C2)OC)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2,4-dimethoxyphenyl)benzamide (203.4 mg, 0.40 mmol) and acetic anhydride (0.046 ml, 0.49 mmol), the procedure of Inventive Example 94 was repeated to obtain 161.2 mg (73.6%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methylphenyl)benzamide (285.0 mg, 0.62 mmol) and acetic anhydride (0.071 ml, 0.74 mmol), the procedure of Inventive Example 94 was repeated to obtain 311.8 mg (99.9%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(phenyl)benzamide (503.8 mg, 1.13 mmol) and acetic anhydride (0.128 ml, 1.36 mmol), the procedure of Inventive Example 94 was repeated to obtain 309.9 mg (71.0%) of the title compound in a light brown amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-trifluoromethylphenyl)benzamide (243.0 mg, 0.474 mmol) and acetic anhydride (0.13 ml, 1.40 mmol), the procedure of Inventive Example 94 was repeated to obtain 265.0 mg quantitative) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)C(F)(F)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-trifluoromethylphenyl)benzamide (256.0 mg, 0.474 mmol) and acetic anhydride (0.13 ml, 1.40 mmol), the procedure of Inventive Example 94 was repeated to obtain 267.0 mg (96.2%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (150.0 mg, 0.335 mmol) and acetic anhydride (0.038 ml, 0.40 mmol), the procedure of Inventive Example 94 was repeated to obtain 151.0 mg (95.6%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 2-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.0 mg, 0.50 mmol) and acetic anhydride (0.057 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 170.4 mg (65.9%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(=O)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)C(=O)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxycarbonylphenyl)benzamide (291.0 mg, 0.58 mmol) and acetic anhydride (0.11 ml, 1.16 mmol), the procedure of Inventive Example 94 was repeated to obtain 303.0 mg (96.0%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=C(C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:CC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-3-methyl-N-{2-[4-(4-fluorobenzoyl)piperidino]-ethyl}-N-(3-methoxyphenyl)benzamide (489.0 mg, 1.00 mmol) and acetic anhydride (0.19 ml, 2.00 mmol), the procedure of Inventive Example 94 was repeated to obtain 474.0 mg (89.3%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=C(C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)OC;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:COC=1C=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1NC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-3-methoxy-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (253.0 mg, 0.50 mmol) and acetic anhydride (0.095 ml, 1.00 mmol), the procedure of inventive Example 94 was repeated to obtain 213.0 mg (77.9%) of the title compound in a yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=CC=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methylphenyl)benzamide (452.7 mg, 0.99 mmol) and acetic anhydride (0.122 ml, 1.19 mmol), the procedure of Inventive Example 94 was repeated to obtain 473.6 mg (95.4%) of the title compound in a light brown amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC=1C=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1, Reagents are:, and Products are 0:C(C)(=O)NC=1C=C(C(=O)N(C2=CC=CC=C2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(phenyl)benzamide (126.4 mg, 0.28 mmol) and acetic anhydride (0.03 ml, 0.32 mmol), the procedure of Inventive Example 94 was repeated to obtain 101.1 mg (73.1%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m1:NC=1C=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methylphenyl)benzamide (230.1 mg, 0.50 mmol) and acetic anhydride (0.057 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 245.2 mg (97.8%) of the title compound in a light yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC=1C=C(C(=O)N(C2=CC=C(C=C2)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC=1C=C(C(=O)N(C2=CC=C(C=C2)F)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-fluorophenyl)benzamide (223.2 mg, 0.48 mmol) and acetic anhydride (0.055 ml, 0.58 mmol), the procedure of inventive Example 94 was repeated to obtain 238.6 mg (98.3%) of the title compound in a light yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC=1C=C(C(=O)N(C2=CC(=CC=C2)SC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC=1C=C(C(=O)N(C2=CC(=CC=C2)SC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 3-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methylthiophenyl)benzamide (196.7 mg, 0.40 mmol) and acetic anhydride (0.046 ml, 0.48 mmol), the procedure of Inventive Example 94 was repeated to obtain 172.2 mg (80.7%) of the title compound in a light brown amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=CC=C(C(=O)N(C2=CC(=C(C=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=C(C=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3,4-dimethylphenyl)benzamide (333.1 mg, 0.70 mmol) and acetic anhydride (0.080 ml, 0.85 mmol), the procedure of Inventive Example 94 was repeated to obtain 359.9 mg (99.7%) of the title compound in a light brown amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC(=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC(=C2)C)C)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3,5-dimethylphenyl)benzamide (382.8 mg, 0.81 mmol) and acetic anhydride (0.092 ml, 0.99 mmol), the procedure of Inventive Example 94 was repeated to obtain 360.9 mg (86.4%) of the title compound in a light brown amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC(C)=O;m1:NC1=CC=C(C(=O)N(C2=CC3=C(C=C2)OCO3)CCN3CCC(CC3)C(C3=CC=C(C=C3)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC3=C(C=C2)OCO3)CCN3CCC(CC3)C(C3=CC=C(C=C3)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3,4-methylenedioxyphenyl)benzamide (245.0 mg, 0.501 mmol) and acetic anhydride (0.057 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 210.3 mg (79.0%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{3-[4-(4-fluorobenzoyl)piperidino]propyl}-N-(3-methoxyphenyl)benzamide (300.0 mg, 0.61 mmol) and acetic anhydride (0.069 ml, 0.73 mmol), the procedure of inventive Example 94 was repeated to obtain 312.6 mg (96.5%) of the title compound in a light yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(CC)(=O)Cl, Reagents are:, and Products are 0:C(CC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.0 mg, 0.50 mmol) and propionyl chloride (0.077 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 240.0 mg (90.4%) of the title compound in a yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(CCCC)(=O)Cl, Reagents are:, and Products are 0:C(CCCC)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.0 mg, 0.50 mmol) and valeryl chloride (0.071 ml, 0.60 mmol), the procedure of Inventive Example 94 was repeated to obtain 232.0 mg (83.0%) of the title compound in a yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C(C)(C)C)(=O)Cl, Reagents are:, and Products are 0:C(C(C)(C)C)(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (200.0 mg, 0.42 mmol) and pivaloyl chloride (0.062 ml, 0.51 mmol), the procedure of Inventive Example 94 was repeated to obtain 214.6 mg (91.2%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:CS(=O)(=O)Cl, Reagents are:, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]-ethyl}-N-(2-methoxyphenyl)benzamide (60 mg, 0.123 mmol) and methanesulfonyl chloride (11 μl, 0.142 mmol), the procedure of Inventive Example 94 was repeated to obtain 40 mg (57.5%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:CS(=O)(=O)Cl;m1:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (50.0 mg, 0.11 mmol) and methanesulfonyl chloride (0.025 ml, 0.316 mmol), the procedure of Inventive Example 94 was repeated to obtain 29.5 mg (50.7%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:CS(=O)(=O)Cl, Reagents are:, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)NS(=O)(=O)C)=O)C2=CC(=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (475.0mg, 1.00 mmol) and methanesulfonyl chloride (0.12 ml, 1.50 mmol), the procedure of inventive Example 94 was repeated to obtain 527.8 mg (95.4%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:ClC(=O)OCC;m1:NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)OC(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (60 mg, 0.123 mmol) and ethyl chloroformate (13 μl, 0.136 mmol), the procedure of Inventive Example 94 was repeated to obtain 50 mg (72.7%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:ClC(=O)OCC, Reagents are:, and Products are 0:C(C)OC(=O)NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (185.0 mg, 0.39 mmol) and ethyl chloroformate (0.11 ml, 1.17 mmol), the procedure of Inventive Example 94 was repeated to obtain 80.0 mg (37.5%) of the title compound in a colorless oily form. |
Here is a chemical reaction formula: Reactants are:m2:C(=O)(OC(C)(C)C)N[C@@H](C)C(=O)O;m4:C([O-])(O)=O.[Na+];m1_m5:NCC1=CC=C(C(=O)N(CCOC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m3:CCN=C=NCCCN(C)C.Cl, Reagents are:m6:O;m1_m5:C(Cl)Cl, and Products are 0:C(C)(C)(C)OC(=O)N[C@H](C(=O)NCC1=CC=C(C(=O)N(CCOC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyethyl)benzamide (120 mg, 0.245 mmol) was dissolved in methylene chloride (5 ml) to which were subsequently added Boc-L-alanine (46.4 mg, 0.245 mmol) and EDC hydrochloride (52 mg, 0.270 mmol) while cooling in an ice bath. After 4 hours of stirring at the same temperature, the reaction solution was mixed with water (10 ml), adjusted to pH 8 with saturated sodium bicarbonate aqueous solution and then extracted with methylene chloride. Thereafter, the resulting organic layer was dried on anhydrous sodium carbonate, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate) to obtain 109 mg (68.9%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:FC(C(=O)O)(F)F;m1_m3:C(C)(C)(C)OC(=O)N(C)CC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC=C(C=C2)CNC)=O)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-(N-tert-Butoxycarbonyl-N-methylamino)methyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (144 mg, 0.239 mmol) was dissolved in methylene chloride (4 ml) to which was subsequently added dropwise trifluoroacetic acid (0.4 ml) while cooling in an ice bath. After 2 hours of stirring at the same temperature, the solvent was removed by evaporation, and the resulting residue was diluted with methylene chloride (10 ml), washed with saturated sodium bicarbonate aqueous solution and saturated brine, and then dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation to obtain 119 mg (98.9%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(C)(C)N=C=O;m1:NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(C)(C)(C)NC(NC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (77.7 mg, 0.164 mmol) and tertbutyl isocyanate (0.022 ml, 0.196 mmol), the procedure of inventive Example 144 was repeated to obtain 72.9 mg (77.6%) of the title compound in a colorless oily form. |
Here is a chemical reaction formula: Reactants are:m4:[OH-].[Na+];m1_m5:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m3:C([O-])(O)=O.[Na+];m2:[O-]C#N.[K+], Reagents are:m1_m5:C(C)(=O)O.O, and Products are 0:N(C(=O)N)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (237.2 mg, 0.50 mmol) was dissolved in acetic acid-water (1:2, 1.8 ml) to which was subsequently added dropwise an aqueous solution (0.5 ml) of potassium cyanate (81.1 mg, 0.90 mmol) After 3 hours of stirring at room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution, alkanized with 10% sodium hydroxide aqueous solution and then extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) and recrystallized from ethyl acetate-ether to obtain 125.6 mg (48.4%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[NH4+];m3:CI;m1_m5:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:[H-].[Na+], Reagents are:m1_m5:C1CCOC1, and Products are 0:CCC(=O)NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) was dissolved in THF (3.0 ml) to which were subsequently added 60% sodium hydride {28.0 mg, 0.70 mmol) and methyl iodide (0.060 ml, 1.00 mmol) at room temperature, followed by 2 hours of stirring. The reaction solution was mixed with saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was recrystallized from methanol-ether to obtain 128.0 mg (80.4%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m2:COC1OC(CC1)OC;m1_m3:NC1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:m1_m3:C(C)(=O)O, and Products are 0:N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC=C(C=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(4-methoxyphenyl)benzamide (237.0 mg, 0.50 mmol) was dissolved in acetic acid (5.0 ml), and the solution was mixed with 2,5-dimethoxytetrahydrofuran (0.065 ml, 0.50 mmol) and heated for 1 hour under reflux. After cooling, acetic acid was distilled off under a reduced pressure, the residue was dissolved in ethyl acetate, and the organic layer was washed with water and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was distilled off under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 217.0 mg (82,7%) of the title compound in a colorless amorphous form. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:COC1OC(CC1)OC, Reagents are:, and Products are 0:N1(C=CC=C1)C1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (238.1 mg, 0.50 mmol) and 2,5-dimethoxytetrahydrofuran (0.066 ml, 0.50 mmol), the procedure of Inventive Example 149 was repeated to obtain 205.0 mg (78.0%) of the title compound in a light brown amorphous form. |
Here is a chemical reaction formula: Reactants are:m3:C([O-])(O)=O.[Na+];m5_m2:B(Br)(Br)Br;m1_m4:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:m5_m2:C(Cl)Cl;m1_m4:C(Cl)Cl, and Products are 0:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)O)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (50.0 mg, 0.10 mmol) was dissolved in methylene chloride (3.0 ml) to which was subsequently added a methylene chloride solution (1 ml) of boron tribromide (0.018 ml, 0.19 mmol) at 0° C. After 12 hours of stirring at 0° C. to room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, and dried on anhydrous sodium sulfate. Thereafter, the solvent was distilled off under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (ethyl acetate-chloroform:methanol=10:1) to obtain 37.3 mg (76.7%) of the title compound in a light yellow amorphous form. |
Here is a chemical reaction formula: Reactants are:m1_m6:[N+](=O)([O-])C1=CC=C(C(=O)NC=2C=NC=CC2)C=C1;m2:[H-].[Na+];m5:[Cl-].[Na+];m4:[I-].[Na+];m3:ClCCN1CCC(CC1)C(C1=CC=CC=C1)=O, Reagents are:m1_m6:CN(C)C=O;m7:CN(C)C=O, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In an atmosphere of argon, 4-nitro-N-(3-pyridyl)benzamide (973 mg, 4.00 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (176 mg, 60%, 4.40 mmol) at room temperature, stirred for 1 hour at 60° C., and added dropwise 1-(2-chloroethyl)-4-benzoylpiperidine (1.38 g, 5.49 mmol) and a catalytically effective amount of a DMF solution (12 ml) of sodium iodide. After 4 hours of stirring at 60° C., the reaction solution was mixed with saturated sodium chloride aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by recrystallization (ethyl acetate-ether) to obtain 439.6 mg (24.0%) of the title compound in a light yellow powder form. |
Here is a chemical reaction formula: Reactants are:m2:N1=CC=CC=C1;m4:C([O-])(O)=O.[Na+];m3:FC(C(=O)O)(F)F;m1_m5:NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:m1_m5:C(Cl)Cl, and Products are 0:FC(C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (229.3 mg, 0.51 mmol) was dissolved in methylene chloride (2.0 ml) to which were subsequently added pyridine (0.05 ml, 0.62 mmol) and anhydrous trifluoroacetic acid (0.09 ml, 0.64 mmol) at 0° C. After 3 hours of stirring at 0° C. to room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with chloroform. The resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1) to obtain 224.8 mg (81.2%) of the title compound in a light yellow powder form. |
Here is a chemical reaction formula: Reactants are:m2:N1=CC=CC=C1;m4:C([O-])(O)=O.[Na+];m1_m5:NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m3:C(C1=CC=CC=C1)(=O)Cl, Reagents are:m1_m5:C(Cl)Cl, and Products are 0:C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (225.3 mg, 0.50 mmol) was dissolved in methylene chloride (2.0 ml) to which were subsequently added pyridine (0.05 ml, 0.62 mmol) and benzoyl chloride (0.09 ml, 0.77 mmol). After 14 hours of stirring at room temperature, the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with chloroform. The resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=20:1) and recrystallization (ethyl acetate-ether) to obtain 196.3 mg (70.6%) of the title compound in a light brown powder form. |
Here is a chemical reaction formula: Reactants are:m2:C(C1=CC=CC=C1)(=O)Cl;m3:N1=CC=CC=C1;m1:NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1, Reagents are:, and Products are 0:C(C1=CC=CC=C1)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-amino-N-[2-(4-benzoylpiperidino)ethyl]-N-(3-pyridyl)benzamide (210.7 mg, 0.49 mmol), benzoyl chloride (0.07 ml, 0.60 mmol) and pyridine (0.05 ml, 0.62 mmol), the procedure of Inventive Example 165 was repeated to obtain 224.3 mg (85.9%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m2:Cl.CCOCC;m1_m3:FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:Cl.FC1=CC=C(C(=O)C2CCN(CC2)CCN(S(=O)(=O)C2=CCC(C=C2)=NO)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-4-(N-hydroxyimino)-N-(2-methoxyphenyl)benzenesulfonamide (65 mg, 0.12 mmol) was dissolved in methylene chloride (2 ml) to which was subsequently added saturated hydrogen chloride/ether solution (1 ml). After 5 minutes of stirring, the solvent was removed by evaporation, and the resulting residue was solidified in ether (5 ml) and collected by filtration to obtain 69 mg (99.8%) of the title compound in a colorless amorphous powder form. |
Here is a chemical reaction formula: Reactants are:m1_m3:FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1;m2:C(C(=O)O)(=O)O, Reagents are:m1_m3:CO, and Products are 0:C(C(=O)O)(=O)O.FC1=CC=C(C(=O)C2CCN(CC2)CCN(C(C2=CC(=CC=C2)OC)=O)C2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-3-methoxy-N-(2-methoxyphenyl)benzamide (107 mg, 0.218 mmol) was dissolved in methanol (10 ml) to which was subsequently added oxalic acid (19.7 mg, 0.218 mmol). After 5 minutes of stirring at room temperature, methanol was removed by evaporation, and the resulting residue was solidified in ether (5 ml) and collected by filtration to obtain 100 mg (79.2%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m2:C(C(=O)O)(=O)O;m1_m3:N[C@H](C(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C, Reagents are:m1_m3:CO, and Products are 0:C(C(=O)O)(=O)O.C(C(=O)O)(=O)O.N[C@H](C(=O)NCC1=CC=C(C(=O)N(C2=C(C=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-[(S)-2-Aminopropionyl]aminomethyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzamide (84.7 mg, 0.155 mmol) was dissolved in methanol (5 ml) and mixed with oxalic acid (28 mg, 0.311 mmol). After 5 minutes of stirring at room temperature, methanol was removed by evaporation, and the resulting amorphous residue was washed with acetone (5 ml) and collected by filtration to obtain 84 mg (85.1%) of the title compound in a colorless amorphous powder form. |
Here is a chemical reaction formula: Reactants are:m4_m2:C(\C=C\C(=O)O)(=O)O;m1_m3:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:m4_m2:CO;m1_m3:CO, and Products are 0:C(\C=C\C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (282.4 mg, 0.55 mmol) was dissolved in methanol (1.5 ml) and mixed with a methanol solution (3.0 ml) of fumaric acid (63.8 mg, 0.55 mmol) at 0° C. Thereafter, the thus precipitated crystals were collected by filtration and washed with ether to obtain 278.3 mg (80.0%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m1:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(C(O)C(O)C(=O)O)(=O)O, Reagents are:, and Products are 0:C(C(O)C(O)C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) and tartaric acid (35.0 mg, 0.30 mmol), the procedure of Inventive Example 211 was repeated to obtain 143.0 mg (75.3%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m2:C(\C=C/C(=O)O)(=O)O;m1:C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(\C=C/C(=O)O)(=O)O.C(C)(=O)NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-acetylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (155.0 mg, 0.30 mmol) and maleic acid (45.0 mg, 0.30 mmol), the procedure of Inventive Example 211 was repeated to obtain 164.0 mg (82.0%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m4_m2:C(\C=C/C(=O)O)(=O)O;m1_m3:NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1, Reagents are:m4_m2:C(C)O;m1_m3:C(C)O, and Products are 0:C(\C=C/C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=CC=C2)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Amino-N-[2-(4-benzoylpiperidino)ethyl]-N-(3-pyridyl)benzamide (3.00 g, 7.00 mmol) was dissolved in ethanol (10.0 ml) to which was subsequently added a ethanol solution (20.0 ml) of maleic acid (812.0 mg, 7.00 mmol) at room temperature, and then stirred. After the solvent was removed by evaporation, the thus precipitated crystals were collected by filtration and washed with ether, and then purified by recrystallization from ethanol-water mixed solution to obtain 2.476 g (65%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m4_m2:C(\C=C\C(=O)O)(=O)O;m1_m3:NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:m4_m2:CO;m1_m3:CO, and Products are 0:C(\C=C\C(=O)O)(=O)O.NC1=CC=C(C(=O)N(C2=CC(=CC=C2)OC)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C2=CC(=CC=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Amino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-methoxyphenyl)benzamide (475.0 mg, 1.00 mmol) was dissolved in methanol (4.0 ml) and mixed with a methanol solution (3.0 ml) of fumaric acid (58.0 mg, 0.50 mmol) at 0° C. Thereafter, the thus precipitated crystals were collected by filtration and recrystallized from an ethanol-water mixture solution to obtain 481.0 mg (90.0%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m1:C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(\C=C\C(=O)O)(=O)O, Reagents are:, and Products are 0:C(\C=C\C(=O)O)(=O)O.C(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-formylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (208.8 mg, 0.44 mmol) and fumaric acid (25.8 mg, 0.22 mmol), the procedure of Inventive Example 271 was repeated to obtain 122.2 mg (52.1%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m1:C(CCCC)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1;m2:C(\C=C\C(=O)O)(=O)O, Reagents are:, and Products are 0:C(\C=C\C(=O)O)(=O)O.C(CCCC)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(CCCC)(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-valerylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]-ethyl}-N-(3-pyridyl)benzamide (139.4 mg, 0.26 mmol) and fumaric acid (15.4 mg, 0.13 mmol), the procedure of inventive Example 271 was repeated to obtain 128.5 mg (84.0%) of the title compound in a light brown amorphous powder form. |
Here is a chemical reaction formula: Reactants are:m2:C(\C=C\C(=O)O)(=O)O;m1:CNC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(\C=C\C(=O)O)(=O)O.CNC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CNC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-methylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (209.5 mg, 0.45 mmol) and fumaric acid (26.7 mg, 0.23 mmol), the procedure of Inventive Example 271 was repeated to obtain 184.9 mg (79.2%) of the title compound in a light brown powder form. |
Here is a chemical reaction formula: Reactants are:m2:C(\C=C\C(=O)O)(=O)O;m1:CS(=O)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(\C=C\C(=O)O)(=O)O.CS(=O)(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.CS(=O)(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-methanesulfonylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (216.8 mg, 0.41 mmol) and fumaric acid (24.3 mg, 0.21 mmol), the procedure of Inventive Example 271 was repeated to obtain 103.4 mg (43.3%) of the title compound in a light brown powder form. |
Here is a chemical reaction formula: Reactants are:m2:C(\C=C\C(=O)O)(=O)O;m1:C(C)OC(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(\C=C\C(=O)O)(=O)O.C(C)OC(=O)NC1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.C(C)OC(=O)NC1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-ethoxycarbonylamino-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (121.9 mg, 0.24 mmol) and fumaric acid (14.0 mg, 0.12 mmol), the procedure of Inventive Example 271 was repeated to obtain 103.8 mg (75.0%) of the title compound in a light yellow amorphous powder form. |
Here is a chemical reaction formula: Reactants are:m2:C(\C=C\C(=O)O)(=O)O;m1:N(C(=O)N)C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1, Reagents are:, and Products are 0:C(\C=C\C(=O)O)(=O)O.N(C(=O)N)C1=CC=C(C(=O)N(C=2C=NC=CC2)CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=C1.N(C(=O)N)C1=CC=C(C(=O)N(CCN2CCC(CC2)C(C2=CC=C(C=C2)F)=O)C=2C=NC=CC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 4-ureido-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(3-pyridyl)benzamide (174.1 mg, 0.36 mmol) and fumaric acid (20.8 mg, 0.18 mmol), the procedure of Inventive Example 271 was repeated to obtain 111.3 mg (56.3%) of the title compound in a colorless powder form. |
Here is a chemical reaction formula: Reactants are:m3:[Si](C)(C)(C(C)(C)C)Cl;m1_m2_m4_m5:OC1C=CC(C1)=O;m1_m2_m4_m5:C(C)N(CC)CC, Reagents are:m1_m2_m4_m5:O1CCCC1;m1_m2_m4_m5:CN(C1=CC=NC=C1)C;m6:O1CCCC1, and Products are 0:O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4-hydroxy-2-cyclopentenone (191 g, 1.95 mol, prepared in example 1) and triethylamine (430 mL, 3.09 mol) in anhydrous tetrahydrofuran (1L) is treated with 4-dimethylaminopyridine (4.90 g, 40.0 mmol). The solution is cooled to 0° C. and treated portionwise, over 10 minutes, with tert-butyldimethylsilyl chloride (278 g, 1.84 mol) maintaining the temperature at or below 10° C. The reaction is then allowed to stir overnight at room temperature. It is then poured into aqueous HCl (0.5N, 1L). The phases are separated and the aqueous phase is extracted with heptane (2×1L). The organic phase and organic extracts are combined, washed with aqueous HCl (0.5N, 2×500 mL), then 5% sodium bicarbonate (500 mL), then brine (500 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum (40° C., 20 mmHg) to provide the title compound (325 g). This is purified by Kugelrohr distillation (70°-80° C., 1 mmHg) to provide the title compound (282 g, 72% yield) as a light yellow oil, Rf =0.55, 20% ethyl acetate/hexane, GC retention time is 14.97 minutes; 1H NMR (CDCl3) δ7.48 (dd, J=5.7, 2.4 Hz, 1H), 6.20 (d, J=5.7 Hz, 1H), 4.95-4.99 (m, 1H), 2.72 (dd, J=18.2, 6.0 Hz, 1H), 2.25 (dd, J=18.2, 2.3 Hz, 1H), 0.88 (s, 9H), 0.11 (s, 6H); 13C NMR (CDCl3) δ 206.4, 163.8, 134.4, 70.8, 44.9, 25.7, 25.6, 18.0; IR (neat) νmax 2957, 2931, 2887, 2858, 1725 cm-1 ; MS (EI) m/e (% relative intensity) 212 (M+, 5), 155 (M+ -57,100). |
Here is a chemical reaction formula: Reactants are:m3:[H-].[Al+3].[Li+].[H-].[H-].[H-];m4:COC(C)(C)C;m1_m5_m2:O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O;m1_m5_m2:[I-].[Li+], Reagents are:m1_m5_m2:CCCCCCC, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mechanically stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (50.2 g, 236 mmol) in anhydrous toluene (1L) under an atmosphere of argon is treated with lithium iodide (160 g, 1.20 mol). The mixture is cooled to -20° C. and treated with lithium aluminum hydride (9.0 g, 237 mmol) in one portion. The reaction is then stirred for 5 minutes and anhydrous tert-butyl methyl ether (200 mL) is added at a rate that maintains the temperature of the reaction at or below -15° C. (total addition time is approximately 3 minutes). The reaction is stirred for one hour at -20° C. and then it is quenched by slow addition of aqueous sodium hydroxide (1N, 250 mL) at a rate that maintains the temperature of the reaction below 20° C. The resulting suspension is then filtered through a pad of diatomaceous earth and the pad is subsequently rinsed with toluene (400 mL). The filtrate phases are separated and the aqueous phase is extracted with toluene (300 mL). The organic phase and organic extract are combined, rinsed with aqueous sodium hydroxide (1N, 300 mL), brine (300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum (40° C., 20 mmHg). The residue is then purified by Kugelrohr distillation (60°-80° C., 1 mmHg) to provide the title compound (37.4 g, 74% yield) as a colorless oil; cis/trans/1-2+1-4 addition, 95.3/2.1/2.6; Rf =0.20, 20% ethyl acetate/hexane, GC retention time for the title compound is 13.95 minutes, while GC retention times for the byproducts corresponding to compounds 3 (trans) and 4 (1-2+1-4 addition) in Scheme I wherein Pg is a TBDMS group are 14.45 min. and 14.06 min. respectively; for the title compound, 1H NMR (CDCl3)δ 5.93 (dt, J=5.5, 1.7 Hz, 1H), 5.84 (dr, J=5.5, 1.6 Hz, 1H), 4.63-4.68 (m, 1H), 4.52-4.62 (m, 1H), 2.76-2.86 (bs, 1H), 2.69 (dr, J=13.8, 7.1 Hz, 1H), 1.52 (dt, J=13.8, 4.7 Hz, 1H), 0.90 (s, 9H), 0.09 (s, 6H); 13C NMR (CDCl3) δ 136.7, 135.6, 75.1, 75.0, 44.5, 25.9, 18.1; IR (neat) νmax 3373, 2957, 2932 cm-1 ; MS (EI) m/e (% relative intensity) 157 (M+ -57). |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O;m1_m5_m2:[I-].[Li+];m3:[H-].[Al+3].[Li+].[H-].[H-].[H-];m4:COC(C)(C)C, Reagents are:m1_m5_m2:C1(=CC=CC=C1)C, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mechanically stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (175 g, 824 mmol) in anhydrous toluene (1.5L) under an atmosphere of argon is treated with lithium iodide (240 g, 1.79 mol). The mixture is cooled to -20° C. and treated with lithium aluminum hydride (13.5 g, 356 mmol) in one portion. The reaction is then stirred for 5 minutes and anhydrous tert-butyl methyl ether (300 mL) is added at a rate that maintains the temperature of the reaction at or below -15° C. (total addition time is approximately 3 minutes). The reaction is stirred for 3 hours at -20° C. and then it is quenched by slow addition of aqueous sodium hydroxide (1N, 250 mL) at a rate that maintains the temperature of the reaction below 20° C. The resulting suspension is then filtered through a pad of diatomaceous earth and the pad is subsequently rinsed with toluene (400 mL). The filtrate phases are separated and the aqueous phase is extracted with toluene (450 mL). The organic phase and organic extract are combined, rinsed with aqueous sodium hydroxide (1N, 450 mL), brine (450 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum (40° C., 20 mmHg). The residue is then purified by Kugelrohr distillation (60°-80° C., 1 mmHg) to provide the title compound (120 g, 68% yield) as a colorless oil; cis/trans/1-2 +1-4 addition, 92/4/4. |
Here is a chemical reaction formula: Reactants are:m3:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m4_m2:O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O;m1_m4_m2:[I-].[Li+], Reagents are:m1_m4_m2:C(C)OCC, and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mechanically stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (1.01 g, 4.76 mmol) in anhydrous ethyl ether (20 mL) under an atmosphere of argon is treated with lithium iodide (3.20 g, 23.9 mmol). The mixture is cooled to -78° C. and treated with lithium aluminum hydride (184 mg, 4.85 mmol) in one portion. The reaction is then stirred for 90 minutes. It is then quenched by slow addition of aqueous sodium hydroxide (1N, 23 mL) at a rate that maintains the temperature of the reaction below 20° C. The resulting suspension is then filtered through a pad of diatomaceous earth and the pad is subsequently rinsed with ether. The filtrate phases are separated and the aqueous phase is extracted with ether (20 mL). The organic phase and organic extract are combined, rinsed with aqueous sodium hydroxide (1N, 20 mL), brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum (40° C., 20 mmHg). The residue is then purified by Kugelrohr distillation (60°-80° C., 1 mmHg) to provide the title compound. (820 mg, 80% yield) as a colorless oil; cis/trans/1-2+1-4 addition, 88.5/3.3/8.2. |
Here is a chemical reaction formula: Reactants are:m3:[OH-].[Na+];m2:[H-].[Al+3].[Li+].[H-].[H-].[H-];m4_m1:O([Si](C)(C)C(C)(C)C)C1C=CC(C1)=O, Reagents are:m4_m1:[Cl-].[Cl-].[Zn+2], and Products are 0:[Si](C)(C)(C(C)(C)C)O[C@H]1C=C[C@H](C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred solution of ZnCl2 (19 mL, 19 mmol, 1M in ether) is treated with 4-tert-butyldimethylsiloxy-2-cyclopentenone (2.0 g, 9.42 mmol) under an atmosphere of argon. The solution is cooled to -20° C. and treated dropwise with lithium aluminum hydride (9.0 mL, 9.0 mmol, 1M in ether) at such a rate as to keep the reaction temperature at or below -15° C. After stirring for about 2 hours at -20° C., approximately 5 mL of 1N NaOH was added. The reaction is filtered through diatomaceous earth, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (1.3 g); cis/trans/1-2+1-4 addition 81/3/16. |