US 11,939,322 B2
Method for producing tetracyclic compound
Hiroki Serizawa, Tokyo (JP); Akira Kawase, Tokyo (JP); Hiroshi Fukuda, Tokyo (JP); and Naoto Hama, Tokyo (JP)
Assigned to Chugai Seiyaku Kabushiki Kaisha, Tokyo (JP)
Appl. No. 17/271,437
Filed by Chugai Seiyaku Kabushiki Kaisha, Tokyo (JP)
PCT Filed Sep. 3, 2019, PCT No. PCT/JP2019/034543
§ 371(c)(1), (2) Date Feb. 25, 2021,
PCT Pub. No. WO2020/050241, PCT Pub. Date Mar. 12, 2020.
Claims priority of application No. 2018-165313 (JP), filed on Sep. 4, 2018.
Prior Publication US 2022/0372025 A1, Nov. 24, 2022
Int. Cl. C07D 413/04 (2006.01)
CPC C07D 413/04 (2013.01) 13 Claims
 
1. A method for manufacturing Compound (1):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, the method comprising a step of manufacturing a compound represented by Formula IXa:

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, by treating a compound represented by Formula VIIIb:

OG Complex Work Unit Chemistry
wherein R1a represents 4-(morpholin-4-yl)piperidin-1-yl group, iodo group, or bromo group; and R2 represents an ethyl group,
with a condensing agent selected from N,N′-diisopropylcarbodiimide and diethyl chlorophosphate in a solvent selected from dichloromethane, 1,4-dioxane, 2-methyltetrahydrofuran, 2-butanone, tert-butyl methyl ether, ethyl acetate, isopropyl acetate, dimethyl sulfoxide, tetrahydrofuran, acetone, and acetonitrile.