Oxalic Acid → (E)-5-Methoxy-1-(2-pyridyl)-2-[2-(3-methyl-2-thienyl)ethenyl]-1H-benzimidazole oxalate

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Reaction Steps

Free base of the titled compound was prepared from 4-methoxy-2-amino-N-(2-pyridyl)aniline and (E)-3-(3-methyl-2-thienyl)acryloyl chloride (Sekiya, T.; Hiranuma, H.; Hata, S.; Mizogami, S.; Hanazuka, M.; Yamada, S. J. Med. Chem., 1983, 26, 411) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl MeOH/n-hexane yielded the titled compound. MW: 437.48; mp: 192.5-193.5° C.; 1H-NMR (DMSO) δ: 8.65 (1H, dd, J=4.9, 1.8 Hz), 8.07 (1H, td, J=7.8, 1.9 Hz), 7.87 (1H, d, J=15.6 Hz), 7.62 (1H, d, J=8.1 Hz), 7.52 (1H, dd, J=7.4, 4.9 Hz), 7.37 (1H, d, J=5.1 Hz), 7.24 (1H, d, J=8.9 Hz), 7.16 (1H, d, J=2.3 Hz), 6.86 (1H, d, J=4.9 Hz), 6.79 (1H, dd, J=8.9,2.5 Hz), 6.67 (1H, d, J=15.6 Hz), 3.72 (3H, s), 2.22 (3H, s).

Provenance & Evidence