Triethylamine → 2-(3-methylbutyryl)phenyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

HRID 1359943Notes

Reaction equation

HRID 1359943 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[CH2:9][CH:10]([CH3:12])[CH3:11].[F:14][C:15]1[N:19]([CH3:20])[N:18]=[C:17]([CH3:21])[C:16]=1[C:22](Cl)=[O:23].C(N(CC)CC)C>O1CCCC1>[CH3:12][CH:10]([CH3:11])[CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:22]([C:16]1[C:17]([CH3:21])=[N:18][N:19]([CH3:20])[C:15]=1[F:14])=[O:23])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108668795-Fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chlorideHCID 122976091-(2-Aminophenyl)-3-methylbutan-1-one

Product 1

HCID 587924542-(3-methylbutyryl)phenyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

At room temperature, 355.0 mg (2.0 mmol) of 1-(2-aminophenyl)-3-methylbutan-1-one are added to a solution comprising 388.5 mg (2.2 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and 0.45 ml (3.2 mmol) of triethylamine in 20 ml of tetrahydrofuran. The reaction mixture is stirred at 60° C. for 1.5 h, filtered through silica gel and concentrated. Column chromatography (cyclohexane/ethyl acetate: 3/1) gives 577.7 mg (1.8 mmol, 88% of theory) of N-[2-(3-methylbutyryl)phenyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide of logP (pH=2.3)=3.42.

Workup

  1. filtrationfiltered through silica gel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f000134bfd4d47f89411bbafd0172129
Source dataset
uspto-grants-2011_02
Patent number
US07879760B2

Reaction notes

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