Synthesis of Azilsartan and Its Selected Potential Impurities

Synthesis of angiotensin II AT1 receptor antagonist azilsartan is described. The results include reinvestigation of the described process as well as its novel modification. This new process includes transformation of the CN group into amidoxime moiety by aqueous hydroxylamine, its treatment with alk...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 50; no. 4; pp. 929 - 936
Main Authors Rádl, Stanislav, Černý, Josef, Stach, Jan, Holec, Jan, Píša, Ondřej, Gablíková, Zuzana
Format Journal Article
LanguageEnglish
Published HOBOKEN Blackwell Publishing Ltd 01.07.2013
Wiley
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANGIOTENSIN
II RECEPTOR ANTAGONISTS
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Summary:Synthesis of angiotensin II AT1 receptor antagonist azilsartan is described. The results include reinvestigation of the described process as well as its novel modification. This new process includes transformation of the CN group into amidoxime moiety by aqueous hydroxylamine, its treatment with alkyl chloroformates and a base‐initiated cyclization of the formed (alkoxycarbonyl‐oxy)carbamimidoyl intermediates. Several so far undescribed side‐products were identified and some of them were synthesized and duly characterized as potential impurities.
Bibliography:ArticleID:JHET1783
ark:/67375/WNG-G4GCM6CD-J
istex:F8667E77CE449F64542636F5BBE17618DC092196
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.1783