Isobutylamine → N-tert-Butyl-3-((4-(2-chloro-4-(3-isobutylureido)benzoyl)piperazin-1-yl)methyl)benzamide

Participants

Reaction Steps

3-((4-(4-Amino-2-chlorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (250 mg, 0.625 mmol) and 4-nitrophenol chloroformate (126 mg, 0.625 mmol) were combined and stirred in dichloromethane for 1 hour. Isobutylamine (87.8 mg, 1.2 mol, 0.12 mL) was added and the reaction was stirred for 30 minutes. The reaction mixture was diluted with water and flushed through a hydrophobic frit. The reaction was concentrated under reduced pressure to give a residue, which was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 4% methanol/dichloromethane) to afford the title compound (178.1 mg).

Provenance & Evidence