4-Chloroaniline → 4,6-dimethyl-pyrimidine-5-carboxylic acid {(R)-3-[4-(4-chloro-phenylamino)-piperidin-1-yl]-butyl}-amide

Participants

Role	Name	HCID	Charge
Reactant	4-Chloroaniline	HCID 7812	—
Reactant	4,6-Dimethylpyrimidine-5-carboxylic acid	HCID 14922222	—
Reactant	(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile	HCID 68972438	—
Product	4,6-dimethyl-pyrimidine-5-carboxylic acid {(R)-3-[4-(4-chloro-phenylamino)-piperidin-1-yl]-butyl}-amide	HCID 86602134	86.3%

Reaction Steps

Using general procedure A with 4-chloroaniline (230 mg, 1.80 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (263 mg, 1.58 mmol), then general procedure J and then using general procedure E with the resulting amine and 4,6-dimethyl-pyrimidine-5-carboxylic acid (100 mg, 0.66 mmol) afforded 4,6-dimethyl-pyrimidine-5-carboxylic acid {(R)-3-[4-(4-chloro-phenylamino)-piperidin-1-yl]-butyl}-amide (237 mg, 35% over 3 steps).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07491735B2
Source dataset	uspto-grants-2009_02
ORD ID	ord-f4d3fcfc6d34481b914b271726e57cf4
Source note	uspto-grants-2009_02