US 12,152,028 B2
Methods of preparing heteroaryl-ketone fused azadecalin glucocorticoid receptor modulators
Jeffrey Mark Dener, Menlo Park, CA (US); Hazel Joan Hunt, Menlo Park, CA (US); Travis Lemons, Menlo Park, CA (US); Gary Reid, Menlo Park, CA (US); Kilian Garrec, Menlo Park, CA (US); Thomas C. Stephens, Menlo Park, CA (US); Adam Daisuke Gammack Yamagata, Menlo Park, CA (US); and Yunguo Lu, Menlo Park, CA (US)
Assigned to Corcept Therapeutics Incorporated, Redwood City, CA (US)
Filed by Corcept Therapeutics Incorporated, Menlo Park, CA (US)
Filed on Dec. 22, 2021, as Appl. No. 17/560,048.
Claims priority of application No. PCT/CN2020/139524 (WO), filed on Dec. 25, 2020.
Prior Publication US 2022/0227753 A1, Jul. 21, 2022
Int. Cl. C07D 471/04 (2006.01); A61K 31/4745 (2006.01); A61K 45/06 (2006.01); A61P 1/16 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 31/4745 (2013.01); A61K 45/06 (2013.01); A61P 1/16 (2018.01); C07B 2200/13 (2013.01)] 41 Claims
 
1. A method of preparing a compound of Formula J:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, comprising:
(a) forming a first reaction mixture comprising a compound of Formula IIb:

OG Complex Work Unit Chemistry
 and
a sulfonyl chloride:

OG Complex Work Unit Chemistry
 to prepare the compound of Formula J in a yield of at least 60% and a purity of at least 98%,
wherein
X1 is —CH═ or —N═;
HX is an acid solvate of HBr, or

OG Complex Work Unit Chemistry
wherein R1 is C1-6 alkyl; and
subscript n is from 1 to 4.