US 11,873,289 B2
Pyrazole compounds and preparation thereof
Sunil Sharma, Gurgaon (IN); Dinesh Jangid, Gurgaon (IN); Priyanka Dhaka, Gurgaon (IN); Siddharth Madhwal, Gurgaon (IN); Bharat Kumar, Gurgaon (IN); Kapil Kumar, Gurgaon (IN); Rajdeep Anand, Gurgaon (IN); and Anurag Jain, Gurgaon (IN)
Assigned to MyoKardia, Inc., Brisbane, CA (US)
Appl. No. 16/966,502
Filed by MYOKARDIA, INC., Brisbane, CA (US)
PCT Filed Feb. 1, 2019, PCT No. PCT/IN2019/050076
§ 371(c)(1), (2) Date Jul. 31, 2020,
PCT Pub. No. WO2019/150392, PCT Pub. Date Aug. 8, 2019.
Claims priority of application No. 201811003855 (IN), filed on Feb. 1, 2018; application No. 201811003859 (IN), filed on Feb. 1, 2018; and application No. 201711042921 (IN), filed on May 30, 2018.
Prior Publication US 2021/0053940 A1, Feb. 25, 2021
Int. Cl. C07D 401/12 (2006.01); C07D 231/12 (2006.01); C07D 231/18 (2006.01); B01J 23/72 (2006.01); B01J 27/122 (2006.01)
CPC C07D 401/12 (2013.01) [B01J 23/72 (2013.01); B01J 27/122 (2013.01); C07D 231/12 (2013.01); C07D 231/18 (2013.01)] 32 Claims
 
1. A process for preparation of a compound of formula II,

OG Complex Work Unit Chemistry
wherein R2 is F, C1-C4 alkyl, or C1-C4 haloalkyl,
R3 is, F, C1-C4 alkyl, or C1-C4 haloalkyl,
R4 is C1-C4 alkyl,
R6 is H or a protecting group or a salt thereof, and
R7 is H, Cl or trialkylsilyl,
comprising the steps of:
a) reacting a compound of formula VII with elemental sulfur in the presence of a base, a catalyst and a reducing agent to give a compound of formula VI;

OG Complex Work Unit Chemistry
wherein R3, R4 and R7 are as defined above and L1 is a leaving group;
b) reacting the compound of formula VI with a compound of formula VIII, to give a compound of formula V;

OG Complex Work Unit Chemistry
wherein L2 is a leaving group and R3, R4, R6 and R7 are as defined above; and
c) converting the compound of formula V to the compound of formula II.