Triethylamine → N-(3-Cyano-4-isobutylphenyl)-1-(4-fluorophenyl)-3-methylpyrazole-4-carboxamide

HRID 1744572

반응식

HRID 1744572 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[C:10]([CH3:16])=[N:9]2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH:25]=1)[C:23]#[N:24].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>O.CN(C)C=O>[C:23]([C:22]1[CH:25]=[C:18]([NH:17][C:13]([C:11]2[C:10]([CH3:16])=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:12]=2)=[O:15])[CH:19]=[CH:20][C:21]=1[CH2:26][CH:27]([CH3:28])[CH3:29])#[N:24]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 222279325-Amino-2-(2-methylpropyl)benzonitrileHCID 222280571-(4-fluorophenyl)-3-methyl-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 22228075N-(3-Cyano-4-isobutylphenyl)-1-(4-fluorophenyl)-3-methylpyrazole-4-carboxamide수율 35.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

1-(4-Fluorophenyl)-3-methylpyrazole-4-carboxylic acid (1.5 g), 5-amino-2-isobutylbenzonitrile (1.2 g), triethylamine (2.0 g) and diethyl cyanophosphate (1.2 g) were added to dimethylformamide (15 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was added into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. A mixed solvent of ethyl acetate-n-hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous dimethylformamide to give the title compound (0.9 g), melting point: 178–179° C.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. additionA mixed solvent of ethyl acetate-n-hexane was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from hydrous dimethylformamide

출처 및 근거

ORD 기록
ord-29466eef691b4b4a9665ab182fc32d67
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015218B1

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