Acetaldehyde → HCID 59349428, compound

Participants

Reaction Steps

Acetaldehyde (0.088 g, 2.0 mmol) was weighed out into a dry 25 ml round bottom flask. N5-(1H-benzo[d]imidazol-2-yl)-N4-(2-methyl-4-(piperidin-4-yloxy)phenyl)-1H-imidazole-4,5-dicarboxamide (0.0465 g, 0.1 mmol) was added, followed by a DMF solution (3.0 ml) of sodium triacetoxyborohydride (0.106 g, 0.5 mmol). The reaction mixture was stir 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) to give N5-1H-benzimidazol-2-yl-N4-{4-[(1-ethylpiperidin-4-yl)oxy]-2-methylphenyl}-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, DMSO-d6): δ 9.49 (s, 1H), 8.22 (s, 1H), 7.52 (m, 1H), 7.41 (m, 2H), 7.23 (m, 2H), 6.97 (m, 2H), 4.75 (m, 1H), 3.54 (m, 2H), 3.37 (m, 3H), 3.12 (m, 4H), 2.24 (m, 4H), 1.22 (s, 3H); MS (EI): 488.7 (MH+).

Provenance & Evidence