US 10,392,353 C1 (13,043rd)
Processes for making substituted quinazoline compounds using hydrogen bonding catalysts
Cheol K. Chung, Westfield, NJ (US); Guy R. Humphrey, Hillsborough, NJ (US); Zhijian Liu, Kendall Park, NJ (US); Mark McLaughlin, Summit, NJ (US); Yingju Xu, Edison, NJ (US); and Younong Yu, East Brunswick, NJ (US)
Filed by Merck Sharp & Dohme Corp., Rahway, NJ (US); Cheol K. Chung, Westfield, NJ (US); Guy R. Humphrey, Hillsborough, NJ (US); Zhijian Liu, Kendall Park, NJ (US); Mark McLaughlin, Summit, NJ (US); Yingju Xu, Edison, NJ (US); and Younong Yu, East Brunswick, NJ (US)
Assigned to MERCK SHARP & DOHME LLC, Rahway, NJ (US)
Reexamination Request No. 90/019,744, Nov. 26, 2024.
Reexamination Certificate for Patent 10,392,353, issued Aug. 27, 2019, Appl. No. 15/778,505, May 23, 2018.
PCT Filed Nov. 18, 2016, PCT No. PCT/US2016/062654
§ 371(c)(1), (2) Date May 23, 2018,
PCT Pub. No. WO2017/091453, PCT Pub. Date Jun. 1, 2017.
Claims priority of provisional application 62/259,167, filed on Nov. 24, 2015.
Ex Parte Reexamination Certificate issued on Sep. 30, 2025.
Int. Cl. C07D 239/84 (2006.01)
CPC C07D 239/84 (2013.01)
AS A RESULT OF REEXAMINATION, IT HAS BEEN DETERMINED THAT:
Claim 17 is cancelled.
Claims 1-16 were not reexamined.
1. A process for preparing a compound of Formula (I):

OG Complex Work Unit Chemistry
or a salt thereof, comprising contacting a compound of formula (viii):

OG Complex Work Unit Chemistry
or a salt thereof, with a catalyst of formula (V):

OG Complex Work Unit Chemistry
wherein each occurrence of R5 is independently selected from the group consisting of phenyl; naphthyl and pyridine: wherein each of the phenyl and naphthyl is optionally substituted with one to three substituents independently selected from halogen, —O—C1-C4alkyl, —CN, —NO2, —O-Tf, and C1-C4alkyl, wherein C1-C4 alkyl can be optionally substituted with one to four halogens; and
each occurrence of R6 is independently selected from the group consisting of Tf and Nf;
in a suitable solvent for a time sufficient to form a compound of formula (I);
wherein:
R1 represents up to 3 phenyl group substituents, each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, halo, —CN,—OH and C1-C6, alkoxy;
R2 represents up to 3 phenyl group substituents, each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, halo, —CN,—OH and C1-C6 alkoxy;
R3 represents up to 3 phenyl group substituents, each independently selected from C1-C6 alkyl, C1-C6 haloalkyl, halo, —CN,—OH and C1-C6 alkoxy; and
R4 is C1-C6 alkyl or C3-C7 cycloalkyl.