tert-butyl [3-({2-[(cyclopropylcarbonyl)amino]-1H-benzimidazol-6-yl}oxy)phenyl]carbamate → N-[6-(3-aminophenoxy)-1H-benzimidazol-2-yl]cyclopropanecarboxamide

Participants

Reaction Steps

tert-Butyl [3-({2-[(cyclopropylcarbonyl)amino]-1H-benzimidazol-6-yl}oxy)phenyl]carbamate (1.58 g, 3.88 mmol) was suspended in trifluoroacetic acid (50 mL), and the reaction mixture was heated under reflux for 1 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), and washed with 0.1N hydrochloric acid (100 mL) and saturated aqueous sodium hydrogencarbonate solution (100 mL), successively. The collected aqueous layer was extracted with ethyl acetate (100 mL×2). The collected organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from methanol to give the title compound (1.06 g, 88%) as pale-brown crystals.

Provenance & Evidence