1,2-Dichloroethane → HCID 69070759, compound

Participants

Reaction Steps

DIPEA (0.75 mL, 4.31 mmol) was added at rt to a mixture of 1-[3-(acetylamino)phenyl]-1H-benzimidazole-5-carboxylic acid (0.83 g, 2.8 mmol), EDC (0.81 g, 4.22 mmol), HOBt (0.57 g, 4.22 mmol) in anhydrous DMA (10 mL). The reaction mixture was stirred for 30 min prior to the dropwise addition of 3-aminomethylpyridine (0.57 mL, 5.62 mmol). After stirring for a further 25 h, the solvent was removed in vacuo and the crude material purified by column chromatography over silica gel eluting with 5-15% MeOH in DCM. The product was further purified by recrystallisation from acetone to afford 1-[3-(acetylamino)phenyl]-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide. 1H NMR (400 MHz, DMSO-d6): δ 2.09 (3H, s), 4.54 (d, J=6.0 Hz, 2H), 7.35-7.4 (m, 2H), 7.56 (t, J=8.0 Hz, 1H), 7.62 (d, J=7.6 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.92 (dd, J=8.4 Hz, 1.2 Hz, 1H), 8.04 (t, J=2.0 Hz, 1H), 8.38 (d, J=1.2 Hz, 1H), 8.46 (dd, J=4.8 Hz, 1.6 Hz, 1H), 8.58 (1H, J=1.6 Hz, 1H), 8.68 (s, 1H), 9.21 (t, J=5.6 Hz, 1H), 10.33 (s, 1H); MS (ES+): m/z 386 [MH+]

Provenance & Evidence