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

HRID 382592Notes

Reaction equation

HRID 382592 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]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 13100385(E)-3-(5-methyl-2-thienyl)acryloyl chlorideHCID 227366532-amino-4-methoxy-N-(2-pyridyl)aniline

Product 1

HCID 22736742(E)-5-Methoxy-2-[2-(5-methyl-2-thienyl)ethenyl]-1-(2-pyridyl)-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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.

Workup

  1. concentrationConcentration and recrystallization from MeOH/n-hexane

Sources & evidence

ORD record
ord-60426dc81a4f429fb5be3b19396f0fc9
Source dataset
uspto-grants-2001_10
Patent number
US06310079B1

Reaction notes

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