Ammonium formate → 3-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

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To a solution of ethyl 3-{6-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (24 mg, 52 μmol) in a mixture of ethanol and water (5:1, 6 mL), was added palladium on carbon (50 mg, 10% w/w Pd) and ammonium formate (17 mg, 270 μmol). The suspension was heated to reflux for 2 hours, cooled to room temperature, filtered through a pad of Celite® and the filtrate was evaporated in vacuo. The residue was taken up in hydrochloric acid (20 mL of a 5N solution) was stirred at room temperature for 72 hours, evaporated in vacuo, and the residue was purified by RP-HPLC to afford the title compounds 3-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid, [LCMS (Method A, Mobile Phase II) RT=3.65 min, MH+ 401], and 3-{6-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid, [LCMS (Method A, Mobile Phase II) RT=3.58 min, MH+ 431].

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