Trifluoroacetic acid → 2-(5-Cyclohexyl-3-difluoromethyl-pyrazol-1-yl)-5-methanesulfonyl-pyridine

HRID 1860581Notes

Reaction equation

HRID 1860581 reaction equation
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][N:5]=1)[NH2:3].C(O)(C(F)(F)F)=O.[F:21][CH:22]([F:34])[C:23](=O)[CH2:24][C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=O>C(O)C(F)(F)F>[CH:27]1([C:25]2[N:2]([C:4]3[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:11])=[O:12])=[CH:6][N:5]=3)[N:3]=[C:23]([CH:22]([F:21])[F:34])[CH:24]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 222268132-Hydrazino-5-(methylsulfonyl)pyridine hydrochlorideHCID 230055004,4-Difluoro-1-cyclohexyl-1,3-butanedione

Product 1

HCID 186240942-(5-Cyclohexyl-3-difluoromethyl-pyrazol-1-yl)-5-methanesulfonyl-pyridineYield 49%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

2-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride (448 mg, 2 mmol) and TFA (1.38 mL, 18 mmol) were mixed in trifluoroethanol (10 mL) and stirred for 5 minutes 4,4-Difluoro-1-cyclohexyl-1,3-butanedione (408 mg, 2 mmol) was added. The resulting reaction mixture was heated at reflux temperature for 60 hours. The solvent was then removed in vacuo, and the residue was partitioned between EtOAc and water. The organic layer was washed with brine and concentrated in vacuo. The product was purified by recrystallization from 3:1 of isooctane:methylene chloride to give the title compound (346 mg, 49%).

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. temperaturewas heated
  4. temperatureat reflux temperature for 60 hours
  5. customThe solvent was then removed in vacuo
  6. customthe residue was partitioned between EtOAc and water
  7. washThe organic layer was washed with brine
  8. concentrationconcentrated in vacuo
  9. customThe product was purified by recrystallization from 3:1 of isooctane

Sources & evidence

ORD record
ord-979f70b49e014e379a3dca779c310276
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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