Triethylamine → N-(3-Cyano-4-isobutoxyphenyl)-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamide

HRID 1744561

Reaction equation

HRID 1744561 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[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:14]([C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:12]=2[CH3:13])=[O:16])[CH:19]=[CH:20][C:21]=1[O:26][CH2:27][CH:28]([CH3:29])[CH3:30])#[N:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 42702631-(4-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acidHCID 193660285-Amino-2-isobutoxybenzonitrile

Product 1

HCID 9821873N-(3-Cyano-4-isobutoxyphenyl)-1-(4-fluorophenyl)-5-methylpyrazole-4-carboxamideYield 34.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(4-Fluorophenyl)-5-methylpyrazole-4-carboxylic acid (2 g), 5-amino-2-isobutoxybenzonitrile (1.7 g), triethylamine (2.7 g) and diethyl cyanophosphate (2.2 g) were added to dimethylformamide (20 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. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane to give the title compound (1.2 g), melting point: 177–178° 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. additionDiisopropyl ether was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from a mixed solvent of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b2fd98bfe31741838dc65fa990f303a6
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Linked notes

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