Ammonium formate → Ethyl 3-{5-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

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To a solution of ethyl 3-{5-[(2-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (30 mg, 66 μmol) in a mixture of ethanol and water (4:1, 5 mL), was added palladium on carbon (6.0 mg, 10% w/w Pd) and ammonium formate (20 mg, 317 μmol). The suspension was heated to reflux for 3 hours, then cooled to room temperature, and filtered through a pad of Celite®. The filtrate was evaporated in vacuo to afford the title compound, 1H NMR: (CD3OD), 8.48 (s, 1H), 8.06 (s, 1H), 7.64 (dd, J=7.69, 1.46, 1H), 7.50-7.35 (br, 7H), 7.28-7.24 (m, 1H), 6.82 (dd, J=8.42, 0.73 1H), 6.74-6.70 (m, 1H), 6.18 (dd, J=9.52, 5.86, 1H), 4.09 (1, J=7.32, 2H), 3.66 (dd, J=16.11, 9.52, 1H), 3.51 (dd, J=16.11, 5.86, 1H), 1.13 (t, J=7.32, 3H).

Provenance & Evidence