US 12,459,904 B2
Process for preparing carbamoyloxymethyl triazole cyclohexyl acid compounds
Richard J. Fox, Yardley, PA (US); Carlos A. Guerrero, North Wales, PA (US); Michael Dummeldinger, Plainsboro, NJ (US); Dimitri Skliar, Staten Island, NY (US); Harshkumar Patel, Somerset, NJ (US); Yichen Tan, East Brunswick, NJ (US); David Thomas George, Ewing, NJ (US); Shane McKenna, Pensby (GB); Candice Lee Joe, Metuchen, NJ (US); and Michael J. Smith, Somerset, NJ (US)
Assigned to Bristol-Myers Squibb Company, Princeton, NJ (US)
Appl. No. 17/603,659
Filed by BRISTOL-MYERS SQUIBB COMPANY, Princeton, NJ (US)
PCT Filed Apr. 14, 2020, PCT No. PCT/US2020/028039
§ 371(c)(1), (2) Date Oct. 14, 2021,
PCT Pub. No. WO2020/214545, PCT Pub. Date Oct. 22, 2020.
Claims priority of provisional application 62/834,538, filed on Apr. 16, 2019.
Prior Publication US 2022/0298122 A1, Sep. 22, 2022
Int. Cl. C07D 249/04 (2006.01); C07C 51/09 (2006.01); C07C 51/12 (2006.01); C07C 51/29 (2006.01); C07D 233/60 (2006.01); C07D 401/04 (2006.01)
CPC C07D 249/04 (2013.01) [C07C 51/09 (2013.01); C07C 51/12 (2013.01); C07C 51/29 (2013.01); C07D 233/60 (2013.01); C07D 401/04 (2013.01)] 23 Claims
 
1. A method of making a compound of Formula (VII), or a stereoisomer or a salt thereof:

OG Complex Work Unit Chemistry
wherein Ra is —N(C1-4 alkyl)2,
comprising contacting a compound of Formula (VIII) or a salt thereof:

OG Complex Work Unit Chemistry
in presence of

OG Complex Work Unit Chemistry
and a co-catalyst selected from

OG Complex Work Unit Chemistry
and 4-DMAP, with or without an aqueous base, in Solvent 5 that is a nonpolar solvent, or a solvent mixture thereof;
for a time and at a temperature sufficient for reaction completion to produce the compound of Formula (VII) or a stereoisomer or a salt thereof.