1-(3-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid → 1-(3-Chlorophenyl)-N-{3-cyano-4-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]phenyl}-5-methylpyrazole-4-carboxamide

HRID 1744667Notes

Reaction equation

HRID 1744667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:26]2[CH2:31][CH2:30][N:29]([CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[CH2:28][CH2:27]2)=[C:22]([CH:25]=1)[C:23]#[N:24]>>[Cl:1][C:2]1[CH:3]=[C:4]([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[CH2:31][CH2:30][N:29]([CH:32]5[CH2:33][CH2:34][O:35][CH2:36][CH2:37]5)[CH2:28][CH2:27]4)=[C:22]([C:23]#[N:24])[CH:25]=3)=[O:16])[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 44236721-(3-chlorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acidHCID 219423235-amino-2-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]benzonitrile

Product 1

HCID 222280671-(3-Chlorophenyl)-N-{3-cyano-4-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]phenyl}-5-methylpyrazole-4-carboxamideYield 41%

Procedure

By the reaction and treatment in the same manner as in Example 64 using 1-(3-chlorophenyl)-5-methylpyrazole-4-carboxylic acid (0.8 g) and 5-amino-2-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]benzonitrile (1.0 g), the title compound (0.7 g) was obtained, melting point: 230° C.

Sources & evidence

ORD record
ord-cb63ab7e7b1e45f8b2a1cec7ec8a2101
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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