Development of a Commercial Manufacturing Process for Sotorasib, a First-in-Class KRASG12C Inhibitor

被引：18

作者：

Zhang, Liang ^{[1
]}

Griffin, Daniel J. ^{[1
]}

Beaver, Matthew G. ^{[1
]}

Blue, Laura E. ^{[1
,2
]}

Borths, Christopher J. ^{[1
]}

Brown, Derek B. ^{[1
]}

Caille, Seb ^{[2
]}

Chen, Ying ^{[2
]}

Cherney, Alan H.

Cochran, Brian M. ^{[2
]}

Colyer, John T. ^{[2
]}

Corbett, Michael T. ^{[2
]}

Correll, Tiffany L. ^{[1
]}

Crockett, Richard D. ^{[2
]}

Dai, Xi-Jie ^{[1
]}

Dornan, Peter K. ^{[1
]}

Farrell, Robert P. ^{[2
]}

Hedley, Simon J. ^{[2
]}

Hsieh, Hsiao-Wu ^{[1
]}

Huang, Liang ^{[2
]}

Huggins, Seth ^{[2
]}

Liu, Min ^{[2
]}

Lovette, Michael A. ^{[2
]}

Quasdorf, Kyle ^{[2
]}

Powazinik, William

Reifman, Jonathan ^{[2
]}

Robinson, Jo Anna ^{[2
]}

Sangodkar, Rahul P. ^{[1
]}

Sharma, Sonika ^{[1
]}

Kumar, Srividya Sharvan ^{[1
]}

Smith, Austin G. ^{[2
]}

St-Pierre, Gabrielle ^{[2
]}

Tedrow, Jason S. ^{[2
]}

Thiel, Oliver R. ^{[1
]}

Truong, Jonathan V. ^{[1
]}

Walker, Shawn D. ^{[1
]}

Wei, Carolyn S.

Wilsily, Ashraf

Xie, Yong ^{[1
]}

Yang, Ning ^{[1
]}

Parsons, Andrew T. ^{[1
]}

机构：

[1] Amgen Inc, Pivotal & Commercial Synthet, Cambridge, MA 02142 USA

[2] Amgen Inc, Prepivotal Attribute Sci, Thousand Oaks, CA 91320 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2022年 / 26卷 / 11期

关键词：

atropisomerism; axial chirality; acrylamide; KRAS; Suzuki-Miyaura; POCl3; chlorination; BOC; palladium; cross-coupling; covalent inhibitor; catalysis; AMG; 510;

D O I：

10.1021/acs.oprd.2c00249

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A commercial process to manufacture sotorasib (AMG 510), a first-in-class KRASG12C inhibitor, is described. Development efforts focused on rendering a fit-for-purpose early-phase route into a viable long-term commercial process through the reduction of side reactions to improve yield and product quality, as well as reducing cycle times of crystallization processes by improving particle properties and filtration times. These improvements were key to ensuring clinical supply and commercial launch. The final route consists of five synthetic operations from starting material M-1, including a telescoped two-step sequence, and a final form

引用

页码：3115 / 3125

页数：11

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