2-(benzenesulfonyl)aniline

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: 4-[(2-benzenesulfonylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 94 mg (0.5 mmol) of 2-[(2-benzenesulfonylphenyl)hydrazono]malononitrile, which was derived from 2-(phenylsulfonyl)aniline (233 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 minutes after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 68 mg (20%) of the compound as an orange coloured solid. Precipitate formed in the reaction tube approximately 20 minutes The resulting solid was isolated by filtration washed with ethanol dried

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

実験手順: 4-[(2-benzenesulfonylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 94 mg (0.5 mmol) of 2-[(2-benzenesulfonylphenyl)hydrazono]malononitrile, which was derived from 2-(phenylsulfonyl)aniline (233 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 minutes after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 68 mg (20%) of the compound as an orange coloured solid. Precipitate formed in the reaction tube approximately 20 minutes The resulting solid was isolated by filtration washed with ethanol dried

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of triphosgene (0.084 g, 0.28 mmol) in dichloromethane (1 ml) at 0° C. was slowly added a solution of 2-benzenesulfonylphenylamine (0.2 g, 0.87 mmol) in dichloromethane (1 ml) and the mixture was stirred at 0° C. for 15 minutes. After that, triethylamine (0.17 g, 1.74 mmol) in dichloromethane (2 ml) was added dropwise at 0° C. and the reaction was allowed to stir at room temperature for 3 h. To this solution a mixture of (S)-2-amino-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester hydrochloride (0.35 g, 0.87 mmol) and triethylamine (0.9 g, 0.87 mmol) in dichloromethane (2 ml) was slowly added and the resulting reaction mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Flash Biotage, dichloromethane:ethyl acetate 3:1) to yield the title compound (0.26 g, 50%) as a white solid. to stir at room temperature for 3 h was slowly added the resulting reaction mixture was stirred at room temperature overnight The volatiles were removed under reduced pressure the residue was purified by column chromatography (Flash Biotage, dichloromethane:ethyl acetate 3:1)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of triphosgene (0.084 g, 0.28 mmol) in dichloromethane (1 ml) at 0° C. was slowly added a solution of 2-benzenesulfonylphenylamine (0.2 g, 0.87 mmol) in dichloromethane (1 ml) and the mixture was stirred at 0° C. for 15 minutes. After that, triethylamine (0.17 g, 1.74 mmol) in dichloromethane (2 ml) was added dropwise at 0° C. and the reaction was allowed to stir at room temperature for 3 h. To this solution a mixture of (S)-2-amino-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester hydrochloride (0.35 g, 0.87 mmol) and triethylamine (0.9 g, 0.87 mmol) in dichloromethane (2 ml) was slowly added and the resulting reaction mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Flash Biotage, dichloromethane:ethyl acetate 3:1) to yield the title compound (0.26 g, 50%) as a white solid. to stir at room temperature for 3 h was slowly added the resulting reaction mixture was stirred at room temperature overnight The volatiles were removed under reduced pressure the residue was purified by column chromatography (Flash Biotage, dichloromethane:ethyl acetate 3:1)

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-benzenesulfonylphenylamine (1.88 g, 8.04 mmol) and diphosgene (0.48 ml, 4.02 mmol) in dioxane (25 ml) was heated at 60° C. for 16 h. The solvent was removed under reduced pressure. A solution of the crude isocyanate (8.04 mmol) in dichloromethane (14 ml) was slowly added to a solution of (S)-4-nitrophenylalanine methyl ester hydrochloride (2.31 g, 8.84 mmol) and triethylamine (3.7 ml, 26.52 mmol) in dichloromethane (14 ml) and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (100 ml) and washed with hydrochloric acid 1N (3×50 ml), saturated aqueous NaHCO3 (3×50 ml) and brine (1×50 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield (S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl ester (3.64 g, 94%) that was used in the next step without further purification. The solvent was removed under reduced pressure the resulting reaction mixture washed with hydrochloric acid 1N (3×50 ml), saturated aqueous NaHCO3 (3×50 ml) and brine (1×50 ml) The organic layer was dried (MgSO4) concentrated under reduced pressure

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-benzenesulfonylphenylamine (1.88 g, 8.04 mmol) and diphosgene (0.48 ml, 4.02 mmol) in dioxane (25 ml) was heated at 60° C. for 16 h. The solvent was removed under reduced pressure. A solution of the crude isocyanate (8.04 mmol) in dichloromethane (14 ml) was slowly added to a solution of (S)-4-nitrophenylalanine methyl ester hydrochloride (2.31 g, 8.84 mmol) and triethylamine (3.7 ml, 26.52 mmol) in dichloromethane (14 ml) and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (100 ml) and washed with hydrochloric acid 1N (3×50 ml), saturated aqueous NaHCO3 (3×50 ml) and brine (1×50 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield (S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl ester (3.64 g, 94%) that was used in the next step without further purification. The solvent was removed under reduced pressure the resulting reaction mixture washed with hydrochloric acid 1N (3×50 ml), saturated aqueous NaHCO3 (3×50 ml) and brine (1×50 ml) The organic layer was dried (MgSO4) concentrated under reduced pressure

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

実験手順: 4-[(2-benzenesulfonylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 94 mg (0.5 mmol) of 2-[(2-benzenesulfonylphenyl)hydrazono]malononitrile, which was derived from 2-(phenylsulfonyl)aniline (233 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 minutes after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 68 mg (20%) of the compound as an orange coloured solid. Precipitate formed in the reaction tube approximately 20 minutes The resulting solid was isolated by filtration washed with ethanol dried

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: This compound was prepared using 94 mg (0.5 mmol) of 2-[(2-benzenesulfonylphenyl)-hydrazono]malononitrile, which was derived from 2-(phenylsulfonyl)aniline (233 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 min after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 68 mg (20%) of the title compound as an orange coloured solid. This compound was prepared Precipitate formed in the reaction tube approximately 20 min The resulting solid was isolated by filtration washed with ethanol dried

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

実験手順: This compound was prepared using 94 mg (0.5 mmol) of 2-[(2-benzenesulfonylphenyl)-hydrazono]malononitrile, which was derived from 2-(phenylsulfonyl)aniline (233 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 min after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 68 mg (20%) of the title compound as an orange coloured solid. This compound was prepared Precipitate formed in the reaction tube approximately 20 min The resulting solid was isolated by filtration washed with ethanol dried

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

実験手順: This compound was prepared using 94 mg (0.5 mmol) of 2-[(2-benzenesulfonylphenyl)-hydrazono]malononitrile, which was derived from 2-(phenylsulfonyl)aniline (233 mg, 1.0 mmol) and malononitrile (1.5 mmol) as described in Example 8, and hydrazine hydrate. Precipitate formed in the reaction tube approximately 20 min after the addition of hydrazine hydrate. The resulting solid was isolated by filtration, washed with ethanol, and dried to yield 68 mg (20%) of the title compound as an orange coloured solid. This compound was prepared Precipitate formed in the reaction tube approximately 20 min The resulting solid was isolated by filtration washed with ethanol dried