US 12,281,104 B2
Process for the production of ethyl 3-amino-1-[(3R,4S)-4-cyanotetrahydropyran-3-yl]pyrazole-4-carboxylate through chiral separation of a racemic mixture
Christophe Pierre Alain Chassaing, Schwabenheim (DE); and Karl-Heinz Grimm, Schwabenheim (DE)
Assigned to Intervet Inc., Rahway, NJ (US)
Appl. No. 17/606,248
Filed by Intervet Inc., Madison, NJ (US)
PCT Filed May 1, 2020, PCT No. PCT/EP2020/062180
§ 371(c)(1), (2) Date Oct. 25, 2021,
PCT Pub. No. WO2020/221914, PCT Pub. Date Nov. 5, 2020.
Claims priority of application No. 19172248 (EP), filed on May 2, 2019.
Prior Publication US 2022/0204483 A1, Jun. 30, 2022
Int. Cl. C07D 405/04 (2006.01)
CPC C07D 405/04 (2013.01) 20 Claims
 
1. A process of producing a compound of Formula VI

OG Complex Work Unit Chemistry
from a mixture of enantiomers comprising separating the enantiomers of a racemic mixture of Formula V

OG Complex Work Unit Chemistry
by chiral chromatography using an eluent and a chiral stationary phase selected from amylose tris(3-chloro-4-methylphenylcarbamate) and amylose tris(3-chloro-5-methylphenylcarbamate) wherein the eluent is acetonitrile.