Acetic Anhydride → HCID 178473794, compound

Participants

Reaction Steps

To a solution of 2-[4-(2-piperidin-2-yl-ethoxy)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide (75 mg, 0.21 mmol) and 4-(dimethylamino)pyridine (13 mg, 0.10 mmol) in DMF (0.5 mL) was added acetic anhydride (20 μL, 0.23 mmol). The reaction mixture was stirred for 18 h before additional acetic anhydride (1 equiv.) and DMAP (3 equiv.) were added. After an additional 24 h, HPLC monitoring indicated reaction completion. The crude material was purified by reverse phase HPLC (C18; H2O/CH3CN/0.01% TFA), providing 39 mg (47%) of product. HPLC (Method C): Rt=4.70. MS (ESI+): mass calcd. for C23H26N4O3, 406.20; m/z found, 407.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.18 (s, 1H), 8.03-7.96 (m, 3H), 7.71 (d, J=8.6 Hz, 1H), 7.18 (d, J=9.0 Hz, 1H), 7.13 (d, J=9.0 Hz, 1H), 4.41-4.26 (m, 1H), 4.15-3.94 (m, 1H), 4.04-3.98 (m, 1H), 3.69-3.64 (m, 1H), 2.67-2.60 (m, 1H), 2.41-2.21 (m, 1H), 1.97 (s, 3H), 1.98-1.85 (m, 1H), 1.72-1.52 (m, 5H), 1.48-1.23 (m, 1H).

Provenance & Evidence