3-Methylbenzylamine → 4,6-Dimethyl-pyrimidine-5-carboxylic acid {3-[4-(3-methyl-benzylamino)-piperidin-1-yl]-butyl}-amide

HRID 1711140Notes

Reaction equation

HRID 1711140 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].O=[C:11]1[CH2:16][CH2:15][N:14]([CH:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21]([C:23]2[C:24]([CH3:30])=[N:25][CH:26]=[N:27][C:28]=2[CH3:29])=[O:22])[CH2:13][CH2:12]1>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH:6][CH:11]1[CH2:12][CH2:13][N:14]([CH:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21]([C:23]2[C:24]([CH3:30])=[N:25][CH:26]=[N:27][C:28]=2[CH3:29])=[O:22])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 660153-MethylbenzylamineHCID 594582434,6-Dimethylpyrimidine-5-carboxylic acid [3-(4-oxo-piperidin-1-yl)-butyl]-amide

Product 1

HCID 866295164,6-Dimethyl-pyrimidine-5-carboxylic acid {3-[4-(3-methyl-benzylamino)-piperidin-1-yl]-butyl}-amideYield 72.1%

Procedure

Using general procedure A, 3-methylbenzylamine (30 μL, 0.23 mmol) and 4,6-dimethylpyrimidine-5-carboxylic acid [3-(4-oxo-piperidin-1-yl)-butyl]-amide (66 mg, 0.22 mmol) afforded 4,6-dimethyl-pyrimidine-5-carboxylic acid {3-[4-(3-methyl-benzylamino)-piperidin-1-yl]-butyl}-amide (65 mg, 72%).

Sources & evidence

ORD record
ord-bd2e2ce5ef8c4cdbaa8218d1ce5d7783
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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