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

Participants

Reaction Steps

To a solution of tert-butyl {3-[(2-amino-1H-benzimidazol-6-yl)oxy]phenyl}carbamate (1.30 g, 3.82 mmol) in pyridine (50 mL) were added cyclopropanecarbonyl chloride (1 mL, 11.0 mmol) and N,N-dimethylpyridine-4-amine (21.3 mg, 174 μmol), and the mixture was stirred at room temperature for 16 hr. To the reaction mixture were added methanol (30 mL) and 8N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at the same temperature for 2.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (5 mL) and ethyl acetate (50 mL). This solution was washed with 0.1N hydrochloric acid (50 mL) and saturated aqueous sodium hydrogencarbonate solution (50 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate and diisopropyl ether to give the title compound (1.53 g, 98%) as colorless crystals.

Provenance & Evidence