Highly Regioselective Protecting-Group-Free Synthesis of the Antimalarial Drug MMV693183

MMV693183 is a promising antimalarial drug candidate that works for uncomplicated malaria treatment and resistance management. Herein, we report an efficient and highly regioselective synthesis of MMV693183. This novel synthetic method highlights a three-step route with an overall yield of 46% from...

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Bibliographic Details
Published in:Organic process research & development 2024-01, Vol.28 (1), p.273-280
Main Authors: Khairnar, Pankaj V., Aleshire, Sarah L., Kumar Ongolu, Ravi, Jin, Limei, Laidlaw, Michael G., Donsbach, Kai O., Gupton, B. Frank, Nelson, Ryan C., Shanahan, Charles S.
Format: Article
Language:English
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Summary:MMV693183 is a promising antimalarial drug candidate that works for uncomplicated malaria treatment and resistance management. Herein, we report an efficient and highly regioselective synthesis of MMV693183. This novel synthetic method highlights a three-step route with an overall yield of 46% from readily available starting materials. The key to the success lies in (1) utilizing the subtle difference of the two amino groups in the starting material (S)-propane-1,2-diamine dihydrochloride without amino protection and (2) identifying the L-(+)-tartaric acid as the counter acid for the organic salt formation, yielding the desired regioisomer up to 100:0. The efficient and scalable three-step protocol operates under mild conditions with a high chemo/regioselectivity, providing effective access to MMV693183.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.3c00353