2,5-Difluorobenzenesulfonyl chloride → HCID 178482075, compound

HRID 45851Notes

Reaction equation

HRID 45851 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[C:4]([C:9]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH3:21])[CH:15]=3)=[CH:12][NH:11][N:10]=2)[C:5]([F:8])=[CH:6][CH:7]=1.[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]>N1C=CC=CC=1>[F:22][C:3]1[C:4]([C:9]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH3:21])[CH:15]=3)=[CH:12][NH:11][N:10]=2)=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:1][S:31]([C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[F:23])(=[O:33])=[O:32]

Participants

4

Reactant 2

HCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 178482073HCID 178482073, compound

Product 1

HCID 178482075HCID 178482075, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of {4-[3-(3-amino-2,6-difluoro-phenyl)-1H-pyrazol-4-yl]-pyridin-2-yl}-methyl-amine (144 mg, 0.48 mmol) in anhydrous pyridine (0.2 M), 2,5-difluoro-benzenesulfonyl chloride (64 μL, 0.48 mmol) was added and the reaction mixture was stirred at room temperature under nitrogen atmosphere overnight. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and washed with saturated aqueous NaHCO3. The organic layer was dried over anhydrous sodium sulfate and filtered. The product was isolated by silica gel column chromatography eluting with methanol 5% in methylene chloride (58%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe product was isolated by silica gel column chromatography
  7. washeluting with methanol 5% in methylene chloride (58%)

Sources & evidence

ORD record
ord-09458504bd324644907eb57ba4538f21
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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