Dimethylformamide → N-{4-[4-(2-Dimethylaminoethyl)piperazin-1-yl]-3-cyanophenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

HRID 1744596Notes

Reaction equation

HRID 1744596 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[CH:19]=[N:20][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[C:22]=2[CH3:23])=[O:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)#[N:2].Cl.[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35]Cl.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][N:12]1[CH2:13][CH2:14][N:9]([C:8]2[CH:7]=[CH:6][C:5]([NH:15][C:16]([C:18]3[CH:19]=[N:20][N:21]([C:24]4[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=4)[C:22]=3[CH3:23])=[O:17])=[CH:4][C:3]=2[C:1]#[N:2])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 22227929N-[3-cyano-4-(piperazin-1-yl)phenyl]-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

Product 1

HCID 21018360N-{4-[4-(2-Dimethylaminoethyl)piperazin-1-yl]-3-cyanophenyl}-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamideYield 12.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

N-[3-Cyano-4-(piperazin-1-yl)phenyl]-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide (2 g), 2-dimethylaminoethyl chloride hydrochloride (0.85 g) and potassium carbonate (0.8 g) were added to dimethylformamide (20 ml) and the mixture was stirred at 60° C. for 3 h. The reaction mixture was added into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated under reduced pressure. Ethanol was added to the residue to allow crystallization. The crystals were recrystallized from hydrous ethanol to give the title compound (0.3 g), melting point: 185° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated under reduced pressure
  4. additionEthanol was added to the residue
  5. customcrystallization
  6. customThe crystals were recrystallized from hydrous ethanol

Sources & evidence

ORD record
ord-33fe0ca63589423e8d984c4f9898da47
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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