Process Development and Large-Scale Synthesis of MK-6186, a Non-Nucleoside Reverse Transcriptase Inhibitor for the Treatment of HIV

A new synthetic route has been developed to drug candidate 1, a second-generation NNRTI being developed as a potential treatment of HIV. Regiocontrol in a key alkylation step was achieved by selective N-alkylation of hydrazone 13. After a deprotection and cyclisation sequence, 1 was isolated in six...

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Bibliographic Details
Published in:Organic process research & development 2012-04, Vol.16 (4), p.605-611
Main Authors: Goodyear, Adrian, Linghu, Xin, Bishop, Brian, Chen, Cheng, Cleator, Ed, McLaughlin, Mark, Sheen, Faye J, Stewart, Gavin W, Xu, Yingju, Yin, Jingjun
Format: Article
Language:English
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Summary:A new synthetic route has been developed to drug candidate 1, a second-generation NNRTI being developed as a potential treatment of HIV. Regiocontrol in a key alkylation step was achieved by selective N-alkylation of hydrazone 13. After a deprotection and cyclisation sequence, 1 was isolated in six steps in 35% overall yield from readily available starting materials.
ISSN:1083-6160
1520-586X
DOI:10.1021/op200334x