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

HRID 1726300Notes

Reaction equation

HRID 1726300 reaction equation
[NH2:1][CH2:2][CH2:3][C@H:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[CH3:5].[CH3:21][C:22]1[C:27]([C:28](O)=[O:29])=[C:26]([CH3:31])[N:25]=[CH:24][N:23]=1>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][CH:9]2[CH2:8][CH2:7][N:6]([C@H:4]([CH3:5])[CH2:3][CH2:2][NH:1][C:28]([C:27]3[C:22]([CH3:21])=[N:23][CH:24]=[N:25][C:26]=3[CH3:31])=[O:29])[CH2:11][CH2:10]2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 149222224,6-Dimethylpyrimidine-5-carboxylic acidHCID 68970439(R)-[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-amine

Product 1

HCID 866021414,6-dimethyl-pyrimidine-5-carboxylic acid {(R)-3-[4-(4-methoxy-phenylamino)-piperidin-1-yl]-butyl}-amideYield 91.8%

Procedure

Using general procedure E, [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-amine (see EXAMPLE 230) (1.59 g, 5.48 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (834 mg, 5.48 mmol) afforded 4,6-dimethyl-pyrimidine-5-carboxylic acid {(R)-3-[4-(4-methoxy-phenylamino)-piperidin-1-yl]-butyl}-amide as a white solid (2.07 g, 83%).

Sources & evidence

ORD record
ord-afd401567c664c0dbf35ed2f2fc5f057
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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