Oxalic Acid → (E)-5-Methoxy-2-[2-(5-methyl-2-thienyl)ethenyl]-1-(2-pyridyl)-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[S:22][C:21](/[CH:23]=[CH:24]/[C:25](Cl)=O)=[CH:20][CH:19]=1.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:21]3[S:22][C:18]([CH3:17])=[CH:19][CH:20]=3)=[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-(5-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 MeOH/n-hexane yielded the titled compound. MW: 437.48; mp: 190.0-191.0° C.; 1H-NMR (DMSO) δ: 8.67-8.63 (1H, m), 8.06 (1H, td, J=7.9, 1.9 Hz), 7.79 (1H, d, J=15.6 Hz), 7.59 (1H, d, J=7.9 Hz), 7.54-7.48 (1H, m), 7.22 (1H, d, J=8.7 Hz), 7.12-7.08 (2H, m), 6.77 (1H, dd, J=8.7, 2.5 Hz), 6.71-6.68 (1H, m), 6.66 (1H, d, J=15.6 Hz), 3.72 (3H, s), 2.33 (3H, s).
Workup
- concentrationConcentration and recrystallization from MeOH/n-hexane
Sources & evidence
- ORD record
- ord-6488fff322224bb485786a451d402e5c
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713482B2
Reaction notes
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