1-Hydroxybenzotriazole → N-(1-cyclohexyl-5-piperidin-1-ylmethyl-1H-benzimidazol-2-yl)-3-(1-tetrazolyl) benzamide

Participants

Reaction Steps

To a solution of 1-cyclohexyl-5-piperidin-1-ylmethyl-1H-benzimidazol-2-amine (100 mg, 0.32 mmol, prepared above) and 3-(1-tetrazolyl)-benzoic acid (76 mg, 0.40 mmol) in N,N-dimethylformamide (2 mL) was added 1-hydroxybenzotriazole (57 mg, 0.42 mmol) followed by 1-(3-dimethylaminopropyl)carbodiimide hydrochloride (80 mg, 0.42 mmol). N,N-diisoproplethylamine (100 mg, 0.77 mmol) was then added and the solution was allowed to stir at room temperature. After 18 hr, the reaction mixture was diluted with N,N-dimethylformamide (2 mL) and water (1 mL), filtered, and purified without work-up by preparative scale HPLC. Freeze-drying afforded (N-(1-cyclohexyl-5-piperidin-1-ylmethyl-1H-benzimidazol-2-yl)-3-(1-tetrazolyl) benzamide) as a cream solid (27 mg, 0.056 mmol): 1H NMR (DMSO-d6, 300 MHz) δ 10.20 (s, 1H), 9.30 (broad s, 1H), 8.63 (s, 1H), 8.34 (d, J=10.0 Hz, 1H), 8.02 (d, J=10 Hz, 1H), 7.81-7.64 (m, 2H), 7.64 (s, 1H), 7.33 (d, J=10.0 Hz, 1H), 4.83-4.63 (m, 1H), 4.41-4.29 (m, 2H), 2.99-1.33 (m, 18H). MS: API m/z 485 (M+H+)

Provenance & Evidence