A Greener Approach for the Large-Scale Synthesis of 1,4,5-Trisubstituted Pyrazole, AZD8329

The development of a convenient, safe and scalable process for AZD8329 manufacturing is reported here. Synthesis was achieved in a two-step telescopic process with an excellent overall yield of 75%. In the first step enamine (6) was synthesized with 90% yield through three chemical transformations....

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Bibliographic Details
Published in:Organic process research & development 2014-08, Vol.18 (8), p.947-951
Main Authors: Rangappa, Paramashivappa, Ghosh, Avipsa, Chitrapadi, Smitha, Kantikar, Gajanan, CH, Vinod Kumar, Sythana, Sureshkumar, Manjunath, Sulur G, Nambiar, Sudhir, R, Sridhran
Format: Article
Language:English
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Summary:The development of a convenient, safe and scalable process for AZD8329 manufacturing is reported here. Synthesis was achieved in a two-step telescopic process with an excellent overall yield of 75%. In the first step enamine (6) was synthesized with 90% yield through three chemical transformations. In the next step AZD8329 was synthesized from the reactions of 6 and 4-hydrazinobenzoic acid hydrochloride 7 through two chemical transformations. The process is very efficient and economical, and AZD8329 was manufactured in multikilogram scale. A greener approach is demonstrated through usage of a minimum number of solvents and energy and with process mass intensity (PMI)
ISSN:1083-6160
1520-586X
DOI:10.1021/op5001463