3-(aminomethyl)-N-methylbenzenesulfonamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (Step 2) To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.28 g) and 3-(aminomethyl)-N-methylbenzenesulfonamide obtained in Step 1 (0.36 g) in ethanol (10 ml) was added potassium carbonate (0.25 g) at room temperature, and the mixture was stirred overnight at 70° C. The reaction solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (76 mg). The reaction solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0) 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil the precipitated crystals were collected by filtration recrystallized

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (Step 2) To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.28 g) and 3-(aminomethyl)-N-methylbenzenesulfonamide obtained in Step 1 (0.36 g) in ethanol (10 ml) was added potassium carbonate (0.25 g) at room temperature, and the mixture was stirred overnight at 70° C. The reaction solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (76 mg). The reaction solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0) 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil the precipitated crystals were collected by filtration recrystallized

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

実験手順: (Step 1) To a 40% methylamine methanol solution (5 ml) was added 3-cyanobenzenesulfonyl chloride (0.88 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, saturated brine was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure. 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol, and the mixture was stirred overnight under a hydrogen atmosphere (1 atm). The solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) to give 3-(aminomethyl)-N-methylbenzenesulfonamide (0.38 g) as a colorless oil. The solvent was evaporated under reduced pressure, saturated brine was added the mixture was extracted with ethyl acetate The solvent was evaporated under reduced pressure 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol the mixture was stirred overnight under a hydrogen atmosphere (1 atm) The solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (Step 2) To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.28 g) and 3-(aminomethyl)-N-methylbenzenesulfonamide obtained in Step 1 (0.36 g) in ethanol (10 ml) was added potassium carbonate (0.25 g) at room temperature, and the mixture was stirred overnight at 70° C. The reaction solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (76 mg). The reaction solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0) 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil the precipitated crystals were collected by filtration recrystallized

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

実験手順: (Step 1) To a 40% methylamine methanol solution (5 ml) was added 3-cyanobenzenesulfonyl chloride (0.88 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, saturated brine was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure. 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol, and the mixture was stirred overnight under a hydrogen atmosphere (1 atm). The solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) to give 3-(aminomethyl)-N-methylbenzenesulfonamide (0.38 g) as a colorless oil. The solvent was evaporated under reduced pressure, saturated brine was added the mixture was extracted with ethyl acetate The solvent was evaporated under reduced pressure 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol the mixture was stirred overnight under a hydrogen atmosphere (1 atm) The solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate)

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

実験手順: (Step 1) To a 40% methylamine methanol solution (5 ml) was added 3-cyanobenzenesulfonyl chloride (0.88 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, saturated brine was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure. 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol, and the mixture was stirred overnight under a hydrogen atmosphere (1 atm). The solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) to give 3-(aminomethyl)-N-methylbenzenesulfonamide (0.38 g) as a colorless oil. The solvent was evaporated under reduced pressure, saturated brine was added the mixture was extracted with ethyl acetate The solvent was evaporated under reduced pressure 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol the mixture was stirred overnight under a hydrogen atmosphere (1 atm) The solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate)

反応条件: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (Step 2) To a suspension of 2-cyano-2-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetamide (0.28 g) and 3-(aminomethyl)-N-methylbenzenesulfonamide obtained in Step 1 (0.36 g) in ethanol (10 ml) was added potassium carbonate (0.25 g) at room temperature, and the mixture was stirred overnight at 70° C. The reaction solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0). 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (76 mg). The reaction solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=7:3→1:0) 4N Hydrochloride-ethyl acetate solution (1 ml) was added to the obtained yellow oil the precipitated crystals were collected by filtration recrystallized

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

実験手順: (Step 1) To a 40% methylamine methanol solution (5 ml) was added 3-cyanobenzenesulfonyl chloride (0.88 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, saturated brine was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure. 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol, and the mixture was stirred overnight under a hydrogen atmosphere (1 atm). The solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) to give 3-(aminomethyl)-N-methylbenzenesulfonamide (0.38 g) as a colorless oil. The solvent was evaporated under reduced pressure, saturated brine was added the mixture was extracted with ethyl acetate The solvent was evaporated under reduced pressure 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol the mixture was stirred overnight under a hydrogen atmosphere (1 atm) The solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate)

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

実験手順: (Step 1) To a 40% methylamine methanol solution (5 ml) was added 3-cyanobenzenesulfonyl chloride (0.88 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, saturated brine was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure. 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol, and the mixture was stirred overnight under a hydrogen atmosphere (1 atm). The solution was filtered through celite. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate) to give 3-(aminomethyl)-N-methylbenzenesulfonamide (0.38 g) as a colorless oil. The solvent was evaporated under reduced pressure, saturated brine was added the mixture was extracted with ethyl acetate The solvent was evaporated under reduced pressure 10% Palladium carbon powder (0.46 g) was added to a solution (10 ml) of the residue in ethanol the mixture was stirred overnight under a hydrogen atmosphere (1 atm) The solution was filtered through celite The solvent was evaporated under reduced pressure The residue was purified by basic silica gel column chromatography (ethyl acetate)