Methanol → 2-(4-Hydroxy-2',5'-dimethoxy-biphenyl-3-yl)-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 (0.8 g) in dichloromethane (3 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), 4-hydroxy-2′,5′-dimethoxy-biphenyl-3-carbaldehyde (129.1 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 (217 mg, 84%). 1H NMR (MeOH-d4) δ 2.26 (s, 3H), 2.37-2.72 (12H), 3.73 (s, 3H), 3.77 (s, 3H), 6.80 (m, 1H), 6.94 (s, 1H), 6.95 (m, 1H), 7.03 (d, J=9 Hz, 1H), 7.13 (d, J=9 Hz, 2H), 7.49-7.64 (4H), 7.80 (d, J=9 Hz, 1H), 8.10 (s, 1H), 8.17 (s, 1H). ESI-MS m/z 592 (MH+).

Provenance & Evidence