HCID 178474492, compound → 4-(2-phenylethynyl)-3-(trifluoromethyl)-1H-pyrazol-5-amine

HRID 588586Notes

Reaction equation

HRID 588586 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[C:10]([C:18]([F:21])([F:20])[F:19])=[N:11][NH:12][C:13]=2[NH:14]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)C.[OH-].[Na+]>[C:1]1([C:7]#[C:8][C:9]2[C:10]([C:18]([F:20])([F:21])[F:19])=[N:11][NH:12][C:13]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 178474492HCID 178474492, compound

Product 1

HCID 1785091224-(2-phenylethynyl)-3-(trifluoromethyl)-1H-pyrazol-5-amineYield 84.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-[4-(2-phenylethynyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]acetamide (900 mg, 3.07 mmol) in ethanol (12 mL) and 25% NaOH (9 mL) was heated to 70° C. for 1.5 h. The organic layer was separated and the aqueous extracted with EtOAc (×2). The combined organics were washed with water and the wash extracted with EtOAc. The combined organics were dried over MgSO4, filtered and evaporated, yielding the title compound as a red oil (652 mg) which was used in the subsequent step.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous extracted with EtOAc (×2)
  3. washThe combined organics were washed with water
  4. extractionthe wash extracted with EtOAc
  5. dry with materialThe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d8ced791ad7547849e679f345cd0ac77
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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