Benzaldehyde → HCID 59349389, compound

Participants

Reaction Steps

N5-1H-Benzimidazol-2-yl-N4-(2-methyl-4-{[1-(phenylmethyl)piperidin-4-yl]oxy}phenyl)-1H-imidazole-4,5-dicarboxamide was prepared in a similar manner as N5-1H-benzimidazol-2-yl-N4-{4-[(1-ethylpiperidin-4-yl)oxy]-2-methylphenyl}-1H-imidazole-4,5-dicarboxamide. Benzaldehyde and N5-(1H-benzo[d]imidazol-2-yl)-N4-(2-methyl-4-(piperidin-4-yloxy)phenyl)-1H-imidazole-4,5-dicarboxamide (0.1 mmol) were treated with a DMF solution of sodium triacetoxyborohydride. 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 31 mg of N5-1H-benzimidazol-2-yl-N4-(2-methyl-4-{[1-(phenylmethyl)piperidin-4-yl]oxy}phenyl)-1H-imidazole-4,5-dicarboxamide as its acetate salt. 1H-NMR (400 MHz, DMSO-d6): 12.12 (s, 1H), 8.06 (s, 1H), 7.38 (m, 3H), 7.25 (m, 4H), 7.19 (m, 1H), 7.04 (m, 2H), 6.85 (d, 1H), 6.79 (dd, 1H), 4.34 (m, 1H), 3.43 (s, 2H), 2.60 (m, 2H), 2.44 (t, 2H), 2.18 (s, 3H), 1.88 (m, 2H), 1.58 (m, 2H); MS (EI): 550.9 (MH+).

Provenance & Evidence