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Triethylamine → N-(3-Cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)-3,5-dimethylpyrazole-4-carboxamide

HRID 1744557
Notes
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Reaction equation

HRID 1744557 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)[C:10]([CH3:17])=[N:9]2)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:23]([CH:26]=1)[C:24]#[N:25].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>O.CN(C)C=O>[C:24]([C:23]1[CH:26]=[C:19]([NH:18][C:14]([C:11]2[C:10]([CH3:17])=[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:20]=[CH:21][C:22]=1[O:27][CH2:28][C:29]([CH3:31])([CH3:30])[CH3:32])#[N:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 14913551-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acidHCID 178227345-Amino-2-neopentyloxybenzonitrile

Product 1

HCID 9910036N-(3-Cyano-4-neopentyloxyphenyl)-1-(4-fluorophenyl)-3,5-dimethylpyrazole-4-carboxamideYield 17.1%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(4-Fluorophenyl)-3,5-dimethylpyrazole-4-carboxylic acid (2 g), 5-amino-2-neopentyloxybenzonitrile (1.7 g), triethylamine (1.7 g) and diethyl cyanophosphate (1.4 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. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous methanol to give the title compound (0.6 g), melting point: 174–175° 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. additionn-Hexane was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from hydrous methanol

Sources & evidence

ORD record
ord-f6b948010fd84f129b5136d2335fd4c0
Source dataset
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07015218B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes