3-amino-N-methylbenzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound (9 mg) was prepared starting from 40 mg of 4-(6-bromomethylbenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine and excess 3-amino-N-methylbenzenesulfonamide. MS (m/z, ES+): 429.2 (M+1, 100%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A reaction vessel charged with the prepared N-methyl-3-nitro-benzenesulfonamide (4.2 g, 19.42 mmol) in 150 ml of ethyl acetate was further charged with 450 mg of 10% palladium on carbon. The reaction mixture was stirred under hydrogen atmosphere for 48 h, then was filtered through a pad of silica gel washing with EtOAc, and the filtrate was concentrated under reduced pressure. The free base was acidified to give 2.1 g, (˜11 mmol, 58% yield) of the title compound (a compound of formula (W) wherein R is methyl) as its HCl-salt. was filtered through a pad of silica gel washing with EtOAc the filtrate was concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Methyl-3-aminobenzene sulfonamide (488 mg, 2.62 mmole) was dissolved in a mixture of 10 mL of H2O and 2 mL of conc. H2SO4, and was cooled to −5°. A solution of NaNO2 (207 mg, 3 mmole) in 2 mL of H2O was added dropwise at such a rate that the temperature doesn't exceed 0°. The reaction was stirred for 10 minutes, urea (100 mg) was added, and the reaction was stirred an additional 10 minutes. The cold solution of diazo compound was slowly added with stirring to a 0° solution of Cu(NO3)2 dihydrate (10.3 g, 43 mmole) and Cu2O (363 mg) in 100 mL of H2O. Stirring was continued for 30 minutes as the temperature was allowed to warm to 23°. The heterogeneous reaction was extracted with Et2O, and the extracts were extracted with 0.2N NaOH. The basic extracts were washed with Et2O, acidified, and extracted with CH2Cl2. The extracts were dried, and the solvent removed. The residue was chromatographed on a silica gel column, and elution with 50% EtOAc in hexane gave the titled product, 175 mg (36%). MS (ESI) 188 (MH+). was cooled to −5° the reaction was stirred an additional 10 minutes Stirring was continued for 30 minutes as the temperature to warm to 23° The heterogeneous reaction was extracted with Et2O the extracts were extracted with 0.2N NaOH The basic extracts were washed with Et2O extracted with CH2Cl2 The extracts were dried the solvent removed The residue was chromatographed on a silica gel column, and elution with 50% EtOAc in hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Methyl-3-aminobenzene sulfonamide (488 mg, 2.62 mmole) was dissolved in a mixture of 10 mL of H2O and 2 mL of conc. H2SO4, and was cooled to −5°. A solution of NaNO2 (207 mg, 3 mmole) in 2 mL of H2O was added dropwise at such a rate that the temperature doesn't exceed 0°. The reaction was stirred for 10 minutes, urea (100 mg) was added, and the reaction was stirred an additional 10 minutes. The cold solution of diazo compound was slowly added with stirring to a 0° solution of Cu(NO3)2 dihydrate (10.3 g, 43 mmole) and Cu2O (363 mg) in 100 mL of H2O. Stirring was continued for 30 minutes as the temperature was allowed to warm to 23°. The heterogeneous reaction was extracted with Et2O, and the extracts were extracted with 0.2N NaOH. The basic extracts were washed with Et2O, acidified, and extracted with CH2Cl2. The extracts were dried, and the solvent removed. The residue was chromatographed on a silica gel column, and elution with 50% EtOAc in hexane gave the titled product, 175 mg (36%). MS (ESI) 188 (MH+). was cooled to −5° the reaction was stirred an additional 10 minutes Stirring was continued for 30 minutes as the temperature to warm to 23° The heterogeneous reaction was extracted with Et2O the extracts were extracted with 0.2N NaOH The basic extracts were washed with Et2O extracted with CH2Cl2 The extracts were dried the solvent removed The residue was chromatographed on a silica gel column, and elution with 50% EtOAc in hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of N-methyl-3-nitrobenzene sulfonamide (608 mg, 2.8 mmole) in 30 mL of MeOH and 5 mL of EtOAc was treated with 10% Pd/C (100 mg) and hydrogenated at 1 atmosphere H2 pressure for 16 hours. The catalyst was filtered, and the filtrate evaporated. The residue was dissolved in EtOAc, washed with H2O, dried and the solvent removed, and gave the titled product, 498 mg (96%). MS (ESI) 187 (MH+). The catalyst was filtered the filtrate evaporated The residue was dissolved in EtOAc washed with H2O dried the solvent removed

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound (9 mg) was prepared starting from 40 mg of 4-(6-bromomethylbenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine and excess 3-amino-N-methylbenzenesulfonamide. MS (m/z, ES+): 429.2 (M+1, 100%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A reaction vessel charged with the prepared N-methyl-3-nitro-benzenesulfonamide (4.2 g, 19.42 mmol) in 150 ml of ethyl acetate was further charged with 450 mg of 10% palladium on carbon. The reaction mixture was stirred under hydrogen atmosphere for 48 h, then was filtered through a pad of silica gel washing with EtOAc, and the filtrate was concentrated under reduced pressure. The free base was acidified to give 2.1 g, (˜11 mmol, 58% yield) of the title compound (a compound of formula (W) wherein R is methyl) as its HCl-salt. was filtered through a pad of silica gel washing with EtOAc the filtrate was concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound (9 mg) was prepared starting from 40 mg of 4-(6-bromomethylbenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine and excess 3-amino-N-methylbenzenesulfonamide. MS (m/z, ES+): 429.2 (M+1,100%).

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound (9 mg) was prepared starting from 40 mg of 4-(6-bromomethylbenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine and excess 3-amino-N-methylbenzenesulfonamide. MS (m/z, ES+): 429.2 (M+1,100%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound (9 mg) was prepared starting from 40 mg of 4-(6-bromomethylbenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine and excess 3-amino-N-methylbenzenesulfonamide. MS (m/z, ES+): 429.2 (M+1, 100%).