Benzylamine → 6-(5-amidino-1H-benzimidazol-2-yl)-N-benzylpyridine-4-carboxamide

Participants

Reaction Steps

A mixture comprising 2-(6-amidino-1H-benzimidazol-2-yl)pyridine-4-carboxylic acid (0.02 g, 0.06 mmol), HOBT (0.008 g, 0.07 mmol), PyBOP (0.032 g, 0.07 mmol), DMF (0.5 mL) and N-methylmorpholine (0.013 mL, 0.12 mmol) was shaken for 10 minutes and then benzyl amine (13 μL, 0.12 mmol) was added. The mixture was shaken for approximately 12 hours and combined with a mixture comprising ether and acetonitrile (5 mL) to give a precipitate. The precipitate was isolated by filtration and purified by HPLC to provide 6-(5-amidino-1H-benzimidazol-2-yl)-N-benzylpyridine-4-carboxamide (10 mg, 0.02 mmol); 1H-NMR (300 Mhz, DMSO-d6): 4.5 (d, 2H, J=5.5 Hz), 7.3 (m, 5H), 7.7 (m, 2H), 8.0 (dd, 1H), 8.2 (bs, 1H), 8.8 (s, 1H), 8.9 (m, 3H), 9.3 (s, 2H), 9.6 (t, 1H, J=1.5 Hz); MS (ESI), Calculated for C21H18N6O: 370.4, Found (MH+): 371.1.

Provenance & Evidence