Formaldehyde → HCID 178423582, compound

Participants

Reaction Conditions

Reaction Steps

N4-(5-Bromo-2-methylphenyl)-N5-(7-(piperidin-4-yloxy)-1H-benzo[d]imidazol-2-yl)-1H-imidazole-4,5-dicarboxamide (0.1 mmol) was weighted out into a round bottomed flask and acetonitrile (5 mL) was added and the resulting solution was stirred at 25° C. Formaldehyde (1.0 mmol) and sodium cyanoborohydride (0.32 mmol) was added. The reaction mixture was kept neutral by the addition of acetic acid. After 2 hours, the reaction mixture was concentrated under reduced pressure. The crude product was purified via reverse phase HPLC (aqueous ammonium acetate/acetonitrile) to give N4-(5-bromo-2-methylphenyl)-N5-{7-[(1-methylpiperidin-4-yl)oxy]-1H-benzimidazol-2-yl}-1H-imidazole-4,5-dicarboxamide as a white solid. 1H-NMR (400 MHz, DMSO-d6): δ 8.06 (s, 1H), 7.97 (s, 1H), 7.35 (m, 1H), 7.28 (d, 1H), 7.12 (dd, 1H), 6.99 (m, 1H), 6.67 (m, 1H), 4.67 (m, 1H), 2.32 (m, 4H), 2.19 (s, 3H), 1.89 (m, 5H), MS (EI): 553.3 (MH+).

Provenance & Evidence