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

HRID 1744572

Reaction equation

HRID 1744572 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-29466eef691b4b4a9665ab182fc32d67
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Linked notes

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