(C-phenoxy-N-sulfamoylcarbonimidoyl)oxybenzene

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: A mixture of 4-(2,3-diaminobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (150 mg) and diphenyl N-sulfamoylcarbonimidate (85 mg) in dichloromethane (8 ml) was refluxed for 24 hours under nitrogen. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with water, driver over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1/chloroform:methanol=6:1) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-(2-sulfamoylamino-1H-benzimidazol-4-yl)carbonylaminobenzamide (38 mg). was refluxed for 24 hours under nitrogen extracted with chloroform The organic layer was washed with water, driver over magnesium sulfate evaporated in vacuo The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1/chloroform:methanol=6:1)

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

実験手順: A mixture of 4-(2,3-diaminobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (150 mg) and diphenyl N-sulfamoylcarbonimidate (85 mg) in dichloromethane (8 ml) was refluxed for 24 hours under nitrogen. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with water, driver over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1/chloroform:methanol=6:1) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-(2-sulfamoylamino-1H-benzimidazol-4-yl)carbonylaminobenzamide (38 mg). was refluxed for 24 hours under nitrogen extracted with chloroform The organic layer was washed with water, driver over magnesium sulfate evaporated in vacuo The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1/chloroform:methanol=6:1)

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: To a solution of sulfamide (100.9 mg, 1.05 mmol) in anhydrous acetonitrile (3.3 mL) is slowly added dichlorodiphenoxymethane (269.1 mg, 1.00 mmol) at 0° C. The reaction mixture is stirred at room temperature overnight before removal of the solvent. The residue is purified by chromatography to provide diphenyl sulfamoylcarbonimidate (280.2 mg, 96% yield) as a white solid product; HPLC-MS calculated for C13H12N2O4S (M+H+) 293.1, found 293.1. at 0° C The residue is purified by chromatography

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

実験手順: Diphenyl sulfamoylcarbonimidate, from step A, (0.05 g, 0.17 mmol) and 3-bromoaniline (18 μl, 0.17 mmol) were dissolved in acetonitrile (0.5 ml) and heated to 70° C. for 12 hours. The reaction was concentrated under vacuum to afford phenyl N-3-bromophenyl-N′-sulfamoylcarbamimidate, which was carried on crude to the next reaction. The reaction was concentrated under vacuum

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

実験手順: Dichlorodiphenoxymethane (1 g, 3.72 mmol) and sulfamide (0.72 g, 7.44 mmol) were dissolved in MeCN (10 ml) and stirred at room temperature for 18 hours. The mixture was concentrated under vacuum and purified by flash chromatography (20-40% EtOAc/hexanes) to afford diphenyl sulfamoylcarbonimidate (0.69 g, 2.34 mmol, 63%) as a colorless oil. The mixture was concentrated under vacuum purified by flash chromatography (20-40% EtOAc/hexanes)

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

実験手順: A mixture of 4-(2,3-diaminobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (150 mg) and diphenyl N-sulfamoylcarbonimidate (85 mg) in dichloromethane (8 ml) was refluxed for 24 hours under nitrogen. The reaction mixture was poured into water and extracted with chloroform. The organic layer was washed with water, driver over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1/chloroform:methanol=6:1) to give 3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]-4-(2-sulfamoylamino-1H-benzimidazol-4-yl)carbonylaminobenzamide (38 mg). was refluxed for 24 hours under nitrogen extracted with chloroform The organic layer was washed with water, driver over magnesium sulfate evaporated in vacuo The residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1/chloroform:methanol=6:1)

反応条件: temp:0.00; pressure:0.00; stir: