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

HRID 1860579Notes

Reaction equation

HRID 1860579 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][C:22]([F:35])([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>[CH2:4]([NH:5][CH2:6][CH3:7])[CH3:9].[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]([C:22]([F:21])([F:34])[F:35])[CH:24]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 110314321-Cyclohexyl-4,4,4-trifluoro-butane-1,3-dioneHCID 222268132-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride

Product 2

HCID 8021DiethylamineHCID 113493052-(5-Cyclohexyl-3-trifluoromethyl-pyrazol-1-yl)-5-methanesulfonyl-pyridineYield 86%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent2×

Procedure

2-Hydrazino-5-(methylsulfonyl)pyridine hydrochloride (425.2 mg, 1.9 mmol) and TFA (0.44 mL, 5.7 mmol) were mixed in trifluoroethanol (15 mL) and heated at reflux temperature for 15 minutes 4,4,4-trifluoro-1-cyclohexyl-1,3-butanedione (422 mg, 1.9 mmol) in trifluoroethanol (5 ml) was added. The resulting reaction mixture was heated at reflux temperature for 3 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 flash chromatography using 7:2:0.5 of hexane:diethylamine:methanol to give the title compound (305 mg, 43%).

Workup

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

Sources & evidence

ORD record
ord-bfbd437eff7844bea04917ffc1acdad3
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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