Fit‐for‐Purpose Synthesis of CDK2 Inhibitor GNE‐140

A six‐step, stereoselective synthesis of cyclin‐dependent kinase 2 (CDK2) inhibitor GNE‐140 was developed. The key bonds were assembled through palladium‐catalyzed Negishi cross‐coupling and Buchwald–Hartwig C−N coupling steps. The stereodiad was established through a single‐step, CuH‐catalyzed enon...

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Bibliographic Details
Published in:Helvetica chimica acta 2023-08, Vol.106 (8), p.n/a
Main Authors: Ambrosi, Andrea, Piechowicz, Katarzyna A., Tuck, Tyler A., Xu, Di, Zhang, Haiming, Gosselin, Francis
Format: Article
Language:English
Subjects:
Cross coupling
Cyclin-dependent kinase 2
design of experiment
Kinases
Liquid chromatography
Palladium
process chemistry
reduction
Stereoselectivity
Synthesis
synthetic methods
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Summary:A six‐step, stereoselective synthesis of cyclin‐dependent kinase 2 (CDK2) inhibitor GNE‐140 was developed. The key bonds were assembled through palladium‐catalyzed Negishi cross‐coupling and Buchwald–Hartwig C−N coupling steps. The stereodiad was established through a single‐step, CuH‐catalyzed enone reduction proceeding in >99 : 1 er and 89 : 11 dr. GNE‐140 was obtained in 25 % overall yield with 98.6 A% HPLC purity.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.202300023