Identification of an Unexpected Impurity in a New Improved Synthesis of Lesinurad

An unexpected phenomenon concerning an otherwise common impurity of lesinurad has been observed in the context of synthetic process development. A new industrial process was designed as a chlorine-free process, but the critical chlorinated impurity 10 was surprisingly detected in the isolated produc...

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Bibliographic Details
Published inOrganic process research & development Vol. 22; no. 12; pp. 1861 - 1867
Main Authors Halama, Aleš, Stach, Jan, Rádl, Stanislav, Benediktová, Kristýna
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
synthetic process development
protection of carboxylic acids
lesinurad
brominating agent
bromination
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Summary:An unexpected phenomenon concerning an otherwise common impurity of lesinurad has been observed in the context of synthetic process development. A new industrial process was designed as a chlorine-free process, but the critical chlorinated impurity 10 was surprisingly detected in the isolated product. Because of the structural similarity of the impurity and the product, no efficient separation of 10 by conventional methods (e.g., crystallization) was discovered. The formation of the impurity was explained by a chlorine impurity in a commercial brominating agent. This communication also describes control of the critical impurity.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.8b00316