Sulfuryl chloride → N-{2,4-difluoro-3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-2,5-difluorobenzenesulfonamide

HRID 1843635Notes

Reaction equation

HRID 1843635 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[C:15]([F:22])=[C:16]([NH2:21])[CH:17]=[CH:18][C:19]=2[F:20])=[N:4]1)[CH3:2].[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[S:31](Cl)(=[O:33])=[O:32].S(Cl)(Cl)(=O)=O>N1C=CC=CC=1>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:5]([C:14]2[C:15]([F:22])=[C:16]([NH:21][S:31]([C:25]3[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=3[F:23])(=[O:33])=[O:32])[CH:17]=[CH:18][C:19]=2[F:20])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 671844933-(1-Ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenylamine

Product 1

HCID 44622209N-{2,4-difluoro-3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-2,5-difluorobenzenesulfonamideYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

3-(1-Ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2,4-difluoro-phenylamine (1.146 g, 3.816 mmol) was dissolved in anhydrous pyridine (30 M) under nitrogen atmosphere and cooled to 0° C. 2,5-Difluoro-benzenesulfonyl chloride (0.513 mL, 3.816 mmol, 1 eq) was added and the mixture was allowed to stir at the same temperature. Further additions of sulfonyl chloride (for a total amount of 0.650 mL) were needed to drive the reaction to completion. The reaction mixture was kept at 0° C. overnight and then it was allowed to reach room temperature. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with NaHCO3 saturated aqueous solution. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was slurried in methanol at 50° C. for 10 minutes and the solid was filtered and washed with ethyl ether. After drying at 40° C. for 5 hours 1.13 g of the title compound were obtained as a white solid (62% yield).

Workup

  1. customthe reaction to completion
  2. customto reach room temperature
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with NaHCO3 saturated aqueous solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. waitThe crude product was slurried in methanol at 50° C. for 10 minutes
  9. filtrationthe solid was filtered
  10. washwashed with ethyl ether
  11. dry with materialAfter drying at 40° C. for 5 hours 1.13 g of the title compound

Sources & evidence

ORD record
ord-509b92615f9a47b9b7e298ef8421820c
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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