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

HRID 1726277Notes

Reaction equation

HRID 1726277 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O=[C:10]1[CH2:15][CH2:14][N:13]([C@H:16]([CH3:20])[CH2:17][C:18]#[N:19])[CH2:12][CH2:11]1.[CH3:21][C:22]1[C:27]([C:28](O)=[O:29])=[C:26]([CH3:31])[N:25]=[CH:24][N:23]=1>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]2[CH2:15][CH2:14][N:13]([C@H:16]([CH3:20])[CH2:17][CH2:18][NH:19][C:28]([C:27]3[C:22]([CH3:21])=[N:23][CH:24]=[N:25][C:26]=3[CH3:31])=[O:29])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 78124-ChloroanilineHCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68972438(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

Product 1

HCID 866021344,6-dimethyl-pyrimidine-5-carboxylic acid {(R)-3-[4-(4-chloro-phenylamino)-piperidin-1-yl]-butyl}-amideYield 86.3%

Procedure

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).

Sources & evidence

ORD record
ord-f4d3fcfc6d34481b914b271726e57cf4
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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