US 12,077,528 B2
Preparation method for deuterated macrocyclic compound
Yihan Wang, Guangdong (CN); and Huanyin Li, Guangdong (CN)
Assigned to Shenzhen TargetRx, Inc., Guangdong (CN)
Appl. No. 17/297,050
Filed by Shenzhen TargetRx, Inc., Guangdong (CN)
PCT Filed Nov. 27, 2019, PCT No. PCT/CN2019/121235
§ 371(c)(1), (2) Date May 26, 2021,
PCT Pub. No. WO2020/108522, PCT Pub. Date Jun. 4, 2020.
Claims priority of application No. 201811432993.4 (CN), filed on Nov. 28, 2018.
Prior Publication US 2022/0024908 A1, Jan. 27, 2022
Int. Cl. C07D 413/14 (2006.01); C07D 401/12 (2006.01)
CPC C07D 413/14 (2013.01) [C07D 401/12 (2013.01); C07B 2200/05 (2013.01); C07B 2200/07 (2013.01)] 8 Claims
 
1. A method for preparing a compound of formula (A):

OG Complex Work Unit Chemistry
comprising the step of:
reacting a compound of formula (F) with a compound of formula (E-a) to form a compound of formula (D-a):

OG Complex Work Unit Chemistry
wherein X2 is halogen, and Pg1 is a hydroxy-protecting group;
alternatively, reacting a compound of formula (G) with a compound of formula (E-b) to form a compound of formula (D-b):

OG Complex Work Unit Chemistry
wherein X2 is halogen, and Pg2 is an amino-protecting group.