From Chiral Resolution to Diastereoselective Ellman Chemistry to Biocatalysis: Route Evolution for the Efficient Synthesis of the Tetrahydrobenzoazepine Core of BTK Inhibitor BIIB091-Reference-Cited by-同舟云学术

From Chiral Resolution to Diastereoselective Ellman Chemistry to Biocatalysis: Route Evolution for the Efficient Synthesis of the Tetrahydrobenzoazepine Core of BTK Inhibitor BIIB091

Published:2023-07-18 Issue:8 Volume:27 Page:1463-1473
ISSN:1083-6160
Container-title:Organic Process Research & Development
language:en
Short-container-title:Org. Process Res. Dev.

Author:

Li Chaomin¹^ORCID,Wang Shujun²,Yang Jianxin³,Yuan Cuicui³,Wang Dong³,Shang Deju³,O’Brien Erin M.¹

Affiliation:

1. Chemical Process Development, Biogen, 225 Binney Street, Cambridge, Massachusetts 02142, United States

2. WuXi Chemistry Department, WuXi AppTec (Wuhan) Co., Ltd., No. 666 GaoXin Road, WuHan East Lake High-Tech Development Zone, Wuhan 430223, China

3. WuXi Chemistry Department, WuXi AppTec (Tianjin) Co., Ltd., 168 Nanhai Road, Tianjin Economic-Technological Development Area (TEDA), Tianjin 300457, China

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.oprd.3c00133

Reference23 articles.

1. Discovery and Preclinical Characterization of BIIB091, a Reversible, Selective BTK Inhibitor for the Treatment of Multiple Sclerosis

2. Sulfone Displacement Approach for Large-Scale Synthesis of 4-Chloro-N-(1-methyl-1H-pyrazol-4-yl)pyrimidin-2-amine

3. aHopkins, B. T.; Ma, B.; Chan, T. R.; Sun, L.; Zhang, L.; Kumaravel, G.; Lyssikatos, J. P.; Koch, K.; Miao, H. WO2,015,089,337, 2015.

4. bHopkins, B. T.; Ma, B.; Prince, R.; Marx, I.; Lyssikatos, J. P.; Zheng, F.; Peterson, M.; Patience, D. B. WO2,018,191,577, 2018.

5. cHopkins, B. T.; Ma, B.; Prince, R.; Marx, I.; Schulz, J.; Nevalainen, M. WO2,020,232,330, 2020.