4,4,4-Trifluoro-1-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-1,3-butanedione → 5-(5-(3-Fluoro-4-(1,3-thiazol-4-yl)phenyl)-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide

HRID 394898Notes

Reaction equation

HRID 394898 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)=[C:9]([F:18])[CH:8]=1)=O.Cl.[NH:23]([C:25]1[CH:26]=[CH:27][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[N:29][CH:30]=1)[NH2:24]>C(O)C>[F:18][C:9]1[CH:8]=[C:7]([C:5]2[N:23]([C:25]3[CH:26]=[CH:27][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[N:29][CH:30]=3)[N:24]=[C:3]([C:2]([F:21])([F:20])[F:1])[CH:4]=2)[CH:12]=[CH:11][C:10]=1[C:13]1[N:14]=[CH:15][S:16][CH:17]=1

Participants

4

Reactant 2

HCID 223138014,4,4-Trifluoro-1-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-1,3-butanedioneHCID 223138295-Hydrazino-2-pyridinesulfonamide hydrochloride

Product 1

HCID 178121385-(5-(3-Fluoro-4-(1,3-thiazol-4-yl)phenyl)-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamideYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4,4,4-trifluoro-1-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-1,3-butanedione (503 mg, 1.59 mmol) and 5-hydrazino-2-pyridinesulfonamide hydrochloride (392 mg, 1.74 mmol) in ethanol (22 ml) was stirred at reflux for 28 h. After cooling, the solvent was removed and the residue was added water, extracted with ethyl acetate. The extracts was dried (MgSO4) and concentrated. This was purified on silica gel eluting with ethyl acetate/hexane (1:4/1:3/1:2) to afford 172 mg (23.0%) of the titled compound as a yellow solid.

Workup

  1. temperatureat reflux for 28 h
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. additionthe residue was added water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extracts was dried (MgSO4)
  7. concentrationconcentrated
  8. customThis was purified on silica gel eluting with ethyl acetate/hexane (1:4/1:3/1:2)

Sources & evidence

ORD record
ord-354e011e94014707aeb4211e490f3267
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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