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

被引：24

作者：

Fraunhoffer, Kenneth J. ^{[1
]}

DelMonte, Albert J. ^{[1
]}

Beutner, Gregory L. ^{[1
]}

Bultman, Michael S. ^{[1
]}

Camacho, Kathryn ^{[1
]}

Cohen, Benjamin ^{[1
]}

Dixon, Darryl D. ^{[1
]}

Fan, Yu ^{[1
]}

Fanfair, Dayne ^{[1
]}

Freitag, Adam J. ^{[1
]}

Glace, Andrew W. ^{[1
]}

Gonzalez-Bobes, Francisco ^{[1
]}

Gujjar, Manjunath ^{[2
]}

Haley, Matthew W. ^{[1
]}

Hickey, Matthew R. ^{[1
]}

Ho, Jeanne ^{[1
]}

Iyer, Vidya ^{[1
]}

Maity, Prantik ^{[2
]}

Patel, Sunil ^{[1
]}

Rosso, Victor W. ^{[1
]}

Schmidt, Michael A. ^{[1
]}

Stevens, Jason M. ^{[1
]}

Tan, Yichen ^{[1
]}

Wilbert, Christopher ^{[1
]}

Young, Ian S. ^{[1
]}

Yu, Miao ^{[1
]}

机构：

[1] Bristol Myers Squibb Global Prod Dev & Supply, Chem & Synthet Dev, One Squibb Dr,POB 191, New Brunswick, NJ 08903 USA

[2] Biocon Bristol Myers Squibb Res & Dev Ctr, Chem & Synthet Dev, Biocon Pk,Jigani Link Rd,Bommasandra 4, Bangalore 560099, Karnataka, India

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2019年 / 23卷 / 11期

关键词：

SNAr; chiral auxiliary; TCFH; methylation; sulfolane; ENANTIOSELECTIVE SYNTHESIS; KEY;

D O I：

10.1021/acs.oprd.9b00359

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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%.

引用

页码：2482 / 2498

页数：17

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