US 12,128,033 B2
Synthetic methods for preparation of 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine
Andrew Becker, San Diego, CA (US); and Joel Radisson, Paris (FR)
Assigned to Neurocrine Biosciences, Inc., San Diego, CA (US); and Sanofi, Paris (FR)
Filed by Neurocrine Biosciences, Inc., San Diego, CA (US); and Sanofi, Paris (FR)
Filed on Mar. 14, 2024, as Appl. No. 18/604,836.
Application 18/604,836 is a continuation of application No. 18/009,662, previously published as PCT/IB2021/000403, filed on Jun. 9, 2021.
Claims priority of application No. PCT/IB2020/000575 (WO), filed on Jun. 10, 2020.
Prior Publication US 2024/0238257 A1, Jul. 18, 2024
Int. Cl. A61K 31/426 (2006.01); A61K 9/00 (2006.01); A61K 9/107 (2006.01); A61K 9/28 (2006.01); A61K 9/48 (2006.01); A61K 45/06 (2006.01); A61K 47/10 (2017.01); A61K 47/14 (2017.01); A61K 47/22 (2006.01); A61K 47/26 (2006.01); A61K 47/32 (2006.01); C07D 277/42 (2006.01)
CPC A61K 31/426 (2013.01) [A61K 9/0095 (2013.01); A61K 9/107 (2013.01); A61K 9/28 (2013.01); A61K 9/4833 (2013.01); A61K 45/06 (2013.01); A61K 47/10 (2013.01); A61K 47/14 (2013.01); A61K 47/22 (2013.01); A61K 47/26 (2013.01); A61K 47/32 (2013.01); C07D 277/42 (2013.01); C07B 2200/13 (2013.01)] 18 Claims
 
1. A compound that is 4-(2-chloro-4-methoxy-5-methylphenyl)-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-N-prop-2-ynyl-1,3-thiazol-2-amine (Compound 1):

OG Complex Work Unit Chemistry
wherein the enantiomeric excess (e.e.%) of the compound is at least 99.7%.