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 965987Notes

Reaction equation

HRID 965987 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-42e37695e363475f965fa925e898062c
Source dataset
uspto-grants-2005_10
Patent number
US06951876B2

Reaction notes

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