US 12,404,272 B2
Process for making a PD-1/PD-L1 inhibitor and salts and crystalline forms thereof
Dengjin Wang, Wilmington, DE (US); Daniel Carper, Wilmington, DE (US); Zhongjiang Jia, Kennett Square, PA (US); Bo Shen, Garnet Valley, PA (US); Joseph A. Sclafani, Malvern, PA (US); Robert Wilson, Wilmington, DE (US); Jiacheng Zhou, Newark, DE (US); Osama Suleiman, Cambridge (GB); and Mark Wright, Cambridge (GB)
Assigned to Incyte Corporation, Wilmington, DE (US)
Filed by Incyte Corporation, Wilmington, DE (US)
Filed on Nov. 21, 2023, as Appl. No. 18/516,626.
Application 18/516,626 is a division of application No. 17/520,174, filed on Nov. 5, 2021, granted, now 11,866,434.
Claims priority of provisional application 63/110,792, filed on Nov. 6, 2020.
Prior Publication US 2024/0158395 A1, May 16, 2024
Int. Cl. C07D 471/04 (2006.01)
CPC C07D 471/04 (2013.01) [C07B 2200/13 (2013.01)] 13 Claims
 
1. A process of preparing (R)-1-((7-cyano-2-(3′-((2-(difluoromethyl)-7-((3-hydroxypyrrolidin-1-yl)methyl)pyrido[3,2-d]pyrimidin-4-yl)amino)-2,2′-dimethyl-[1,1′-biphenyl]-3-yl)benzo[d]oxazol-5-yl)methyl) piperidine-4-carboxylic acid (compound of formula 1), or a salt thereof, comprising:
reacting a compound of formula B-2:

OG Complex Work Unit Chemistry
or a salt thereof, with a salt of formula B-3:

OG Complex Work Unit Chemistry
wherein M+ is Li+, Na+, K+, or Cs+, in the presence of a Suzuki catalyst and a base to form a compound of formula A-7:

OG Complex Work Unit Chemistry
or a salt thereof, wherein R1 is C1-6 alkyl and X1b is halo.