US 12,325,707 B2
Process for preparing enantiomerically enriched JAK inhibitors
Robert S. Lewis, Lexington, MA (US); Mahender Reddy Karla, Lexington, MA (US); Kathryn E. Kavouris, Cambridge, MA (US); Yong Dong, Chestnut Hill, MA (US); Adam J. Morgan, Ashland, MA (US); and Cameron J. Cowden, Lexington, MA (US)
Assigned to SUN PHARMACEUTICAL INDUSTRIES, INC., Princeton, NJ (US)
Appl. No. 17/428,850
Filed by Sun Pharmaceutical Industries, Inc., Princeton, NJ (US)
PCT Filed Feb. 6, 2020, PCT No. PCT/US2020/017093
§ 371(c)(1), (2) Date Aug. 5, 2021,
PCT Pub. No. WO2020/163653, PCT Pub. Date Aug. 13, 2020.
Claims priority of provisional application 62/850,981, filed on May 21, 2019.
Claims priority of provisional application 62/802,129, filed on Feb. 6, 2019.
Prior Publication US 2022/0306636 A1, Sep. 29, 2022
Int. Cl. C07D 487/04 (2006.01); C07B 59/00 (2006.01); C07C 309/65 (2006.01); C07D 403/04 (2006.01)
CPC C07D 487/04 (2013.01) [C07B 59/002 (2013.01); C07C 309/65 (2013.01); C07D 403/04 (2013.01)] 19 Claims
 
1. A process for preparing a compound of Formula I:

OG Complex Work Unit Chemistry
or a salt thereof,
the process comprising reacting a compound of
Formula II′:

OG Complex Work Unit Chemistry
or a salt thereof, in the presence of an acid such that a compound of Formula I is formed;
wherein in Formula I and Formula II′,
Y1 is hydrogen or deuterium;
each Y2 is the same and is hydrogen or deuterium;
each Y3 is the same and is hydrogen or deuterium;
and in Formula II′,
each R1′ is C1-C10 alkyl, or C2-C10 alkenyl, or the two R1′s, taken together with the oxygen atoms to which they are attached, form a 5-7-membered heterocyclic ring which may optionally be substituted; and
each R6 is independently selected from H and a protecting group.