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

HRID 1744596노트

반응식

HRID 1744596 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-33fe0ca63589423e8d984c4f9898da47
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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