US 11,713,298 B2
Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid
Boris I. Gorin, Cambridge, MA (US); Christopher M. Lanthier, Cambridge, MA (US); Anne Buu Chau Luong, Cambridge, MA (US); James Densmore Copp, Cambridge, MA (US); and Javier Gonzalez, Cambridge, MA (US)
Assigned to Akebia Therapeutics, Inc., Cambridge, MA (US)
Appl. No. 17/53,614
Filed by Akebia Therapeutics, Inc., Cambridge, MA (US)
PCT Filed May 8, 2019, PCT No. PCT/US2019/031310
§ 371(c)(1), (2) Date Nov. 6, 2020,
PCT Pub. No. WO2019/217550, PCT Pub. Date Nov. 14, 2019.
Claims priority of provisional application 62/669,135, filed on May 9, 2018.
Prior Publication US 2021/0070709 A1, Mar. 11, 2021
Int. Cl. C07D 213/81 (2006.01)
CPC C07D 213/81 (2013.01) 17 Claims
 
1. A process for preparing a compound of Formula (8)

OG Complex Work Unit Chemistry
or a salt thereof, comprising:
contacting a compound of Formula (I) or a salt thereof,

OG Complex Work Unit Chemistry
wherein:
R1 is C1-4 alkyl, CH2Cl, phenyl, or benzyl, in which each of phenyl and benzyl may be independently substituted with one, two or three substituents selected from methyl, methoxy, nitro and halogen; and
R2 is C1-4 alkyl,
with a hydrolyzing agent,
wherein the compound of Formula (I) or a salt thereof is prepared by a process comprising:
a) contacting a compound of Formula (5) or a salt thereof,

OG Complex Work Unit Chemistry
with a compound of Formula (II) or a salt thereof in the presence of a base,

OG Complex Work Unit Chemistry
wherein R1 is C1-4 alkyl, CH2Cl, phenyl, or benzyl, in which each of phenyl and benzyl may be independently substituted with one, two or three substituents selected from methyl, methoxy, nitro and halogen; and
b) contacting a product formed in step a) with a compound of Formula (III) or a salt thereof in the presence of a base,

OG Complex Work Unit Chemistry
wherein R2 is C1-4 alkyl; and
c) washing the compound of Formula (I) from step b) with a solvent comprising water and a base,
to provide the compound of Formula (I) or a salt thereof,

OG Complex Work Unit Chemistry