US 12,215,110 B2
Processes and intermediates for preparing a Btk inhibitor
Philip James Pye, Bridgewater, NJ (US); Andras Horvath, Turnhout (BE); Cheng Yi Chen, San Diego, CA (US); Yuanyuan Yuan, Changzhou (CN); Jinxiong Su, Changzhou (CN); Shuo Wang, Changzhou (CN); and Simon Albert Wagschal, Schaffhausen (CH)
Assigned to Janssen Pharmaceutica NV, Beerse (BE)
Appl. No. 17/612,082
Filed by JANSSEN PHARMACEUTICA NV, Beerse (BE)
PCT Filed May 20, 2020, PCT No. PCT/EP2020/064123
§ 371(c)(1), (2) Date Nov. 17, 2021,
PCT Pub. No. WO2020/234381, PCT Pub. Date Nov. 26, 2020.
Claims priority of application No. PCT/CN2019/087823 (WO), filed on May 21, 2019.
Prior Publication US 2022/0204516 A1, Jun. 30, 2022
Int. Cl. C07D 487/04 (2006.01)
CPC C07D 487/04 (2013.01) 22 Claims
 
1. A process for preparing a compound of formula (I);

OG Complex Work Unit Chemistry
wherein:
R1 is a nitrogen protecting group;
R2 is hydrogen or aryl;
X1 is a leaving group or —N(R3)R4;
at least one of R3 and R4 is a nitrogen protecting group, and the other is hydrogen or an independent nitrogen protecting group;
wherein the process comprises reacting a compound of formula (II);

OG Complex Work Unit Chemistry
with an oxidant and a copper-based catalyst.