Hydrochloric Acid → HCID 178423585, compound

Participants

Reaction Steps

Paraformaldehyde (0.088 g, 2.0 mmol) was weighed out into a dry 25 ml round bottom flask. N4-(5-bromo-2-methylphenyl)-N5-(5-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-imidazole-4,5-dicarboxamide hydrochloride (0.0465 g, 0.1 mmol) was added, followed by sodium triacetoxyborohydride (0.106 g, 0.5 mmol) dissolved in DMF (3.0 ml). The reaction mixture was stirred at room temperature over night (16 hours). The reaction mixture was then treated with 1 mL of 1N hydrochloric acid and concentrated under reduced pressure. The resulting crude material was purified by reverse phase HPLC (ammonium acetate/acetonitrile) which gave N4-(5-bromo-2-methylphenyl)-N5-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, DMSO-d6): δ 9.83 (s, 1H), 8.28 (s, 1H), 7.88 (s, 1H), 7.45 (dd, 1H), 7.30 (m, 2H), 7.12 (m, 1H), 7.05 (m, 1H), 3.77 (d, 2H), 3.56 (d, 2H), 3.21 (d, 2H), 2.97 (m, 2H), 2.89 (s, 3H), 2.30 (s, 3H); MS (EI): 538.7 (MH+).

Provenance & Evidence