1-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid → 1-(4-Chlorophenyl)-N-{3-cyano-4-[4-(N,N-dimethylamino)piperidin-1-yl]phenyl}-5-methylpyrazole-4-carboxamide

HRID 1744603Notes

Reaction equation

HRID 1744603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]([CH3:34])[CH3:33])[CH2:28][CH2:27]2)=[C:22]([CH:25]=1)[C:23]#[N:24]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([N:26]4[CH2:27][CH2:28][CH:29]([N:32]([CH3:33])[CH3:34])[CH2:30][CH2:31]4)=[C:22]([C:23]#[N:24])[CH:25]=3)=[O:16])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 27771661-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acidHCID 222279845-amino-2-[4-(N,N-dimethylamino)piperidin-1-yl]benzonitrile

Product 1

HCID 222282041-(4-Chlorophenyl)-N-{3-cyano-4-[4-(N,N-dimethylamino)piperidin-1-yl]phenyl}-5-methylpyrazole-4-carboxamideYield 30.9%

Procedure

By the reaction and treatment in the same manner as in Example 64 using 1-(4-chlorophenyl)-5-methylpyrazole-4-carboxylic acid (3.3 g) and 5-amino-2-[4-(N,N-dimethylamino)piperidin-1-yl]benzonitrile (2.9 g), the title compound (1.7 g) was obtained, melting point: 210–213° C.

Sources & evidence

ORD record
ord-f9ed713d07f7472d863de7970dec5f35
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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