Sodium Hydroxide → 2-[1,4]diazepan-1-yl-1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazole

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Reaction Steps

Reflux 4-{1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazol-2-yl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester (0.42 g, 0.98 mmol) in ethanol (15 mL) with 57% hydroiodic acid (5 mL) for one hour. Cool, treat with sodium hydroxide solution (final pH 13) and extract with dichloromethane (10×50 mL). Dry the combined organic phases (Na2SO4), filter and concentrate the filtrate in vacuo to afford 2-[1,4]diazepan-1-yl-1-[2-(5-methyl-tetrazol-1-yl)-ethyl]-1H-benzoimidazole (0.27 g), Rf=0.60 (silica gel, dichloromethane:methanol:ammonium hydroxide solution, 80:20:0.2).

Provenance & Evidence