Water → 1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-amine

HRID 1528083Notes

Reaction equation

HRID 1528083 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:21][C:22]([F:25])([F:24])[F:23])(=O)=O.O>CN(C=O)C>[F:23][C:22]([F:25])([F:24])[CH2:21][N:6]1[CH:5]=[C:4]([NH2:1])[CH:8]=[N:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 70159181-(2,2,2-trifluoroethyl)-1H-pyrazol-4-amineYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-nitro-1H-pyrazole (500 mg) and potassium carbonate (1.22 g) in DMF (5 mL) was added dropwise 2,2,2-trifluoroethyl trifluoromethanesulfonate (1.54 g). The reaction mixture was stirred at room temperature for 4 hr, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A suspension of the obtained residue and palladium on carbon (1 g) in methanol (30 mL) was stirred at room temperature for 12 hr under a hydrogen atmosphere, filtered, and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (490 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionA suspension of the obtained residue and palladium on carbon (1 g) in methanol (30 mL)
  5. stirringwas stirred at room temperature for 12 hr under a hydrogen atmosphere
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f2e7ebb6a9934397a0557ac96908ef34
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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