US 12,084,443 B2
Process of preparing a PD-1/PD-L1 inhibitor
Jiacheng Zhou, Newark, DE (US); Zhongjiang Jia, Kennett Square, PA (US); Qiyan Lin, Newark, DE (US); Pingli Liu, Wilmington, DE (US); Yongchun Pan, Wilmington, DE (US); Timothy Martin, Hockessin, DE (US); Bo Shen, Garnet Valley, PA (US); Naijing Su, Hockessin, DE (US); and Yongzhong Wu, Glen Mills, PA (US)
Assigned to Incyte Corporation, Wilmington, DE (US)
Filed by Incyte Corporation, Wilmington, DE (US)
Filed on Aug. 31, 2023, as Appl. No. 18/240,805.
Application 18/240,805 is a division of application No. 17/520,060, filed on Nov. 5, 2021, granted, now 11,780,836.
Claims priority of provisional application 63/110,779, filed on Nov. 6, 2020.
Prior Publication US 2023/0406852 A1, Dec. 21, 2023
Int. Cl. C07D 471/04 (2006.01)
CPC C07D 471/04 (2013.01) 9 Claims
 
1. A process of preparing (R)-1-((7-cyano-2-(3′-((3-(((R)-3-hydroxypyrrolidin-1-yl)methyl)-1,7-naphthyridin-8-yl)amino)-2,2′-dimethyl-[1,1′-biphenyl]-3-yl)benzo[d]oxazol-5-yl)methyl)pyrrolidine-3-carboxylic acid, or a salt thereof, comprising:
reacting a compound of formula III-5:

OG Complex Work Unit Chemistry
or a salt thereof, with a compound of formula IV-1:

OG Complex Work Unit Chemistry
or a salt thereof, in the presence of a Suzuki catalyst and a base to form a compound of formula IV-2:

OG Complex Work Unit Chemistry
or a salt thereof, wherein:
each R3 is independently selected from H and C1-6 alkyl; or
each R3 together form an C2-3 alkylene linker, which is optionally substituted by 1, 2, 3, or 4 independently selected C1-4 alkyl groups; and
R4 is C1-6 alkyl; and
X1 is halo.