5-amino-2-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]benzonitrile → N-{3-Cyano-4-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]phenyl}-1-(3,4-difluorophenyl)-5-methylpyrazole-4-carboxamide

HRID 1744665Notes

Reaction equation

HRID 1744665 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH3:14])=[C:12]([C:15]([OH:17])=O)[CH:11]=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([N:27]2[CH2:32][CH2:31][N:30]([CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH2:29][CH2:28]2)=[C:23]([CH:26]=1)[C:24]#[N:25]>>[C:24]([C:23]1[CH:26]=[C:19]([NH:18][C:15]([C:12]2[CH:11]=[N:10][N:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[C:13]=2[CH3:14])=[O:17])[CH:20]=[CH:21][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH2:29][CH2:28]1)#[N:25]

Participants

3

Reactant 2

HCID 219423235-amino-2-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]benzonitrileHCID 222279151-(3,4-difluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 22227981N-{3-Cyano-4-[4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)piperazin-1-yl]phenyl}-1-(3,4-difluorophenyl)-5-methylpyrazole-4-carboxamideYield 53.7%

Procedure

By the reaction and treatment in the same manner as in Example 64 using 1-(3,4-difluorophenyl)-5-methylpyrazole-4-carboxylic acid (0.7 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 (0.8 g) was obtained, melting point: 235° C.

Sources & evidence

ORD record
ord-d3582e5f1462466d8ce6e2f75f62f7ca
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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