Rapid Development of a Commercial Process for Linrodostat, an Indoleamine 2,3-Dioxygenase (IDO) Inhibitor

Rapid Development of a Commercial Process for Linrodostat, an Indoleamine 2,3-Dioxygenase (IDO) Inhibitor

The process development and the kilogram-scale synthesis of linrodostat (BMS-986205, 1) are described. The synthesis features several highly efficient telescoped processes and the use of Evans auxiliary to install a methyl-bearing stereocenter. The target was prepared in 12 steps with 7 isolations i...

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Veröffentlicht in:Organic process research & development 2019-11, Vol.23 (11), p.2482-2498
Hauptverfasser: Fraunhoffer, Kenneth J, DelMonte, Albert J, Beutner, Gregory L, Bultman, Michael S, Camacho, Kathryn, Cohen, Benjamin, Dixon, Darryl D, Fan, Yu, Fanfair, Dayne, Freitag, Adam J, Glace, Andrew W, Gonzalez-Bobes, Francisco, Gujjar, Manjunath, Haley, Matthew W, Hickey, Matthew R, Ho, Jeanne, Iyer, Vidya, Maity, Prantik, Patel, Sunil, Rosso, Victor W, Schmidt, Michael A, Stevens, Jason M, Tan, Yichen, Wilbert, Christopher, Young, Ian S, Yu, Miao
Format: Artikel
Sprache:eng
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Zusammenfassung:The process development and the kilogram-scale synthesis of linrodostat (BMS-986205, 1) are described. The synthesis features several highly efficient telescoped processes and the use of Evans auxiliary to install a methyl-bearing stereocenter. The target was prepared in 12 steps with 7 isolations in an overall yield of 31%.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.9b00359