1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69070759, compound

Participants

Reaction Steps

To a stirred mixture of 1-[3-(acetylamino)phenyl]-1H-benzimidazole-5-carboxylic acid (0.83 g, 2.8 mmol), EDCI (0.81 g, 4.22 mmol), HOBt (0.57 g, 4.22 mmol) in anhydrous DMA (10 mL) was added DIPEA (0.75 mL, 4.31 mmol) at rt. The reaction mixture was stirred for 0.5 h and then (3-aminomethyl)pyridine (0.57 mL, 5.62 mmol) was added drop-wise. Stirring was continued for an additional 25 h. The solvent was evaporated in vacuo and the crude material was purified by silica gel chromatography (5%-15% MeOH in CH2Cl2) and then recrystallized from acetone to afford 1-[3-(acetylamino)phenyl]-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 2.09 (3H, s), 4.54 (d, J=6.0 Hz, 2H), 7.35-7.40 (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