Alternate Synthesis of Apixaban (BMS-562247), an Inhibitor of Blood Coagulation Factor Xa

An alternate approach to apixaban was described. The synthesis features a novel and cost-effective synthetic strategy to construct a key N-phenylvalerolactam intermediate 4 from 4-nitroaniline. In addition, the modified synthetic route avoids the use of expensive reagents and significantly improves...

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Bibliographic Details
Published inSynthetic communications Vol. 43; no. 1; pp. 72 - 79
Main Authors Jiang, Jian'an, Ji, Yafei
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 01.01.2013
Taylor & Francis
Taylor & Francis Ltd
Subjects
4-nitroaniline
Apixaban
Blood
Chemistry
Chemistry, Organic
Coagulation
cost-effective synthetic route
FDA approval
inhibitor of blood coagulation factor Xa
Physical Sciences
Science & Technology
cost-effective synthetic route
4-nitroaniline
THROMBOSIS
inhibitor of blood coagulation factor Xa
Apixaban
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Summary:An alternate approach to apixaban was described. The synthesis features a novel and cost-effective synthetic strategy to construct a key N-phenylvalerolactam intermediate 4 from 4-nitroaniline. In addition, the modified synthetic route avoids the use of expensive reagents and significantly improves reaction yields. As demonstrated practically, apixaban was successfully synthesized in overall good yield (35%).
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2011.591956