Cyanogen Bromide → N-[methyl]-N-methoxy 1-(cyclopentyl)-2-amino-1H-benzimidazole-6-carboxamide

Participants

Reaction Steps

Combine N-[methoxy]-N-[methyl]3-cyclopentylamino-4-aminobenzamide (1.79 g, 6.82 mmol) and lithium methoxide (0.27 g, 7.16 mmol) in anhydrous dichloromethane (25 mL) and stir for 20 minutes. Add a solution of cyanogen bromide (0.83 g, 7.84 mmol) anhydrous dichloromethane (8 mL) and stir overnight at room temperature under nitrogen. Concentrate under reduced pressure and partition the residue between ethyl acetate and water. Wash the organic layer sequentially saturated aqueous sodium bicarbonate (2×20 mL), saturated aqueous sodium chloride (2×20 mL), and water (2×20 mL). Dry over magnesium sulfate and concentrate under reduced pressure to provide the desired compound as a dark solid (1.62 g, 82%).

Provenance & Evidence