US 9,809,569 B2
Process for producing heterocyclic compound
Masatoshi Yamada, Osaka (JP); Sayuri Hirano, Osaka (JP); Ryoji Tsuruoka, Osaka (JP); and Mitsuhisa Yamano, Osaka (JP)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (JP)
Appl. No. 15/125,299
Filed by Takeda Pharmaceutical Company Limited, Osaka (JP)
PCT Filed Mar. 13, 2015, PCT No. PCT/JP2015/057541
§ 371(c)(1), (2) Date Sep. 12, 2016,
PCT Pub. No. WO2015/137496, PCT Pub. Date Sep. 17, 2015.
Claims priority of application No. 2014-052809 (JP), filed on Mar. 14, 2014.
Prior Publication US 2017/0081305 A1, Mar. 23, 2017
Int. Cl. C07D 401/04 (2006.01); C07D 211/60 (2006.01); C07D 211/78 (2006.01); C07F 17/02 (2006.01); B01J 31/24 (2006.01); C07F 9/50 (2006.01); C07F 15/00 (2006.01); B01J 31/22 (2006.01)
CPC C07D 401/04 (2013.01) [B01J 31/2226 (2013.01); B01J 31/2295 (2013.01); B01J 31/2409 (2013.01); B01J 31/2452 (2013.01); C07D 211/60 (2013.01); C07D 211/78 (2013.01); C07F 9/5027 (2013.01); C07F 15/0046 (2013.01); C07F 17/02 (2013.01); B01J 2231/645 (2013.01); B01J 2531/0205 (2013.01); B01J 2531/0263 (2013.01); B01J 2531/0266 (2013.01); B01J 2531/821 (2013.01); B01J 2531/822 (2013.01); B01J 2531/824 (2013.01); B01J 2531/827 (2013.01); B01J 2531/842 (2013.01); B01J 2540/225 (2013.01); C07B 2200/07 (2013.01)] 4 Claims
 
1. A method of producing an optically active form of a compound represented by the formula:

OG Complex Work Unit Drawing
wherein
R2′, R3′ and R4′ are independently a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group; or
R2′ and R3′ in combination, or R3′ and R4′ in combination optionally form a 5- to 8-membered ring together with the adjacent atoms;
R7 and R8 are independently an optionally substituted hydrocarbon group, a hydrogen atom, or an optionally substituted heterocyclic group; and
the carbon atom marked with * is an asymmetric carbon atom,
or a salt thereof, which comprises reacting an optically active form of a compound represented by the formula:

OG Complex Work Unit Drawing
wherein each symbol is as defined above,
or a salt thereof, with a compound represented by the formula:

OG Complex Work Unit Drawing
wherein
L1 is a leaving group, and
the other symbols are as defined above,
or a salt thereof.