Oxalic Acid → (E)-5-Methoxy-1-(2-pyridyl)-2-[2-(3-methyl-2-thienyl)ethenyl]-1H-benzimidazole oxalate
Reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:5]([NH2:16])[CH:4]=1.[CH3:17][C:18]1[CH:22]=[CH:21][S:20][C:19]=1/[CH:23]=[CH:24]/[C:25](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:51]([OH:56])(=[O:55])[C:52]([OH:54])=[O:53]>C(OCC)(=O)C>[C:51]([OH:56])(=[O:55])[C:52]([OH:54])=[O:53].[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[C:25](/[CH:24]=[CH:23]/[C:19]3[S:20][CH:21]=[CH:22][C:18]=3[CH3:17])=[N:16][C:5]=2[CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- concentrationConcentration and recrystallization from ethyl MeOH/n-hexane
Sources & evidence
- ORD record
- ord-454a0044220244a392fdaba9ee82f39a
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713482B2
Reaction notes
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