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Issue 5, 2020
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Continuous flow synthesis of the URAT1 inhibitor lesinurad

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Abstract

Herein, the urate anion exchange transporter 1 (URAT1) inhibitor lesinurad is synthesized from commercially available building blocks by a five-step linear continuous flow sequence. Our previously developed continuous flow platform was successfully applied to generate the 3-thio-1,2,4-triazole key intermediate 2 in 88% yield, after 55 minutes of residence time. Condensation, cyclization and S-alkylation were telescoped in a single operation without conducting solvent exchanges and intermediate purifications. Next, 1,2,4-triazole bromination and ester hydrolysis were also performed in continuous flow regime to deliver lesinurad in 68% overall yield in a total residence time of 2 hours. Our approach enables the fast generation of lesinurad and can be directly applied to produce major quantities of this important API.

Graphical abstract: Continuous flow synthesis of the URAT1 inhibitor lesinurad

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Article information


Submitted
20 Dec 2019
Accepted
27 Jan 2020
First published
27 Jan 2020

React. Chem. Eng., 2020,5, 865-872
Article type
Paper

Continuous flow synthesis of the URAT1 inhibitor lesinurad

M. C. F. C. B. Damião, H. M. Marçon and J. C. Pastre, React. Chem. Eng., 2020, 5, 865
DOI: 10.1039/C9RE00483A

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