Dimethylamine → 2-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid dimethylamide

Participants

Reaction Steps

To a solution of 2-[2-hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid (containing 1 equivalent of DMA, 44 mg, 0.1 mmol), dimethylamine in THF (0.5 mL, 2 M, 1 mmol) and HATU (38 mg, 0.1 mmol) in DMF (1.5 mL) was added DIEA (26 mg, 0.2 mmol). The reaction mixture was stirred at room temperature for 1 h and heated at 65° C. for 15 h, and then evaporated under reduced pressure. The residue was purified by chromatography (500:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (31 mg, 80%). 1H NMR (MeOH-d4) δ 3.05 (s, 3H), 3.12 (s, 3H), 3.95 (s, 3H), 7.00-7.06 (2H), 7.31 (d, J=9 Hz, 1H), 7.52-7.75 (4H), 8.08-8.14 (2H). ESI-MS m/z 389.5 (MH+).

Provenance & Evidence