Methanol → 2-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid {4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-amide

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Reaction Steps

To a suspension of silica gel (6.0 g) in dichloromethane (20 mL) was added SOCl2 (1.5 mL) and the mixture was stirred at the room temperature for 1 h (gas was released from the reaction mixture). 3,4-Diamino-N-{4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-benzamide (707.0 mg, 2.0 mmol) and 2-hydroxy-5-(2-methoxy-pyridin-3-yl)-benzaldehyde (458.5 mg, 2.0 mmol) were added, and the resulting mixture was stirred at the room temperature for 4 h. After methanol (10 mL) was added, the reaction mixture was stirred at room temperature for another 1 h and was evaporated under reduced pressure. The residue on silica gel was purified by chromatography (250:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (528 mg, 47%). 1H NMR (MeOH-d4) δ 2.25 (s, 3H), 2.35-2.71 (12H), 3.94 (s, 3H), 6.96 (m, 1H), 7.00 (d, J=9 Hz, 1H), 7.11 (d, J=9 Hz, 2H), 7.50-7.60 (4H), 7.66 (d, J=9 Hz, 1H), 7.79 (d, J=9 Hz, 1H), 8.06 (d, J=7 Hz, 1H), 8.10 (s, 1H), 8.14 (s, 1H). ESI-MS m/z 563 (MH+).

Provenance & Evidence