A novel and practical synthesis of substituted 2-ethoxy benzimidazole: candesartan cilexetil

A novel and practical synthetic route for the preparation of candesartan cilexetil from methyl 2-amino-3-nitrobenzoate is described. The key steps are the reaction of methyl 2-bromo-3-(diethoxymethyleneamino)benzoate with (2′-(1-trityl-1 H-tetrazol-5-yl) biphenyl-4-yl) methanamine and the final form...

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Bibliographic Details
Published in:Tetrahedron 2010-07, Vol.66 (29), p.5402-5406
Main Authors: Wang, Ping, Zheng, Guo-jun, Wang, Ya-ping, Wang, Xiang-jing, Li, Yan, Xiang, Wen-sheng
Format: Article
Language:English
Subjects:
Antihypertensive
Candesartan cilexetil
Receptor antagonist
Synthesis
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Summary:A novel and practical synthetic route for the preparation of candesartan cilexetil from methyl 2-amino-3-nitrobenzoate is described. The key steps are the reaction of methyl 2-bromo-3-(diethoxymethyleneamino)benzoate with (2′-(1-trityl-1 H-tetrazol-5-yl) biphenyl-4-yl) methanamine and the final formation of 2-ethoxy benzimidazole ring via intramolecular N-arylation. The final ring closure process could be utilized to prepare other 2-substituted benzimidazoles. The method is simple for operation and suitable for industrial production. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.05.037