Methanol → 2-[2-Hydroxy-5-(6-methoxy-pyridin-2-yl)-phenyl]-1H-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 (0.8 g) in dichloromethane (5 mL) was added SOCl2 (0.6 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 (178.2 mg, 0.5 mmol), 2-hydroxy-5-(6-methoxy-pyridin-2-yl)-benzaldehyde (114.6 mg, 0.5 mmol) and 2 mL dichloromethane were added, and the resulting reaction mixture was stirred at the room temperature for 4 h. After methanol (5 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 (190 mg, 68%). 1H NMR (MeOH-d4) δ 2.26 (s, 3H), 2.37-2.72 (12H), 4.01 (s, 3H), 6.62 (d, J=9 Hz, 1H), 7.04 (d, J=9 Hz, 1H), 7.12 (d, J=9 Hz, 2H), 7.37 (d, J=6 Hz, 1H), 7.55 (d, J=9 Hz, 1H), 7.54-7.63 (2H), 7.76 (d, J=6 Hz, 1H), 8.04 (d, J=6 Hz, 1H), 8.13 (s, 1H), 8.53 (s, 1H). ESI-MS m/z 563 (MH+).

Provenance & Evidence