Diethyl Ether → N-[(2,5-difluorophenyl)sulfonyl]-N-{3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}acetamide

HRID 1631546Notes

Reaction equation

HRID 1631546 reaction equation
[F:1][C:2]1[C:7]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][N:10]([CH2:19][CH3:20])[N:9]=2)=[C:6]([F:21])[CH:5]=[CH:4][C:3]=1[NH:22][S:23]([C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[F:33])(=[O:25])=[O:24].[C:34](Cl)(=[O:36])[CH3:35].C(OCC)C>C(Cl)Cl.O>[F:33][C:27]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=1[S:23]([N:22]([C:3]1[CH:4]=[CH:5][C:6]([F:21])=[C:7]([C:8]2[C:12]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)=[CH:11][N:10]([CH2:19][CH3:20])[N:9]=2)[C:2]=1[F:1])[C:34](=[O:36])[CH3:35])(=[O:24])=[O:25]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 44622209N-{2,4-difluoro-3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-2,5-difluorobenzenesulfonamide

Product 1

HCID 53341262N-[(2,5-difluorophenyl)sulfonyl]-N-{3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]-2,4-difluorophenyl}acetamideYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-{2,4-difluoro-3-[1-ethyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}-2,5-difluorobenzenesulfonamide (80 mg, 0.168 mmol) was suspended in 3.5 mL of DCM and TEA (18.7 mg, 25.8 μL, 0.185 mmol) was added. Acetyl chloride (20.0 mg, 18.0 μL, 0.252 mmol) was added to the solution so obtained, and the reaction mixture was stirred at room temperature overnight, diluted with DCM, and poured in water. The organic layer was washed three times with water, once with brine, dried over Na2SO4 and concentrated to dryness. The solid so obtained was taken up with ethyl ether and filtered (79 mg, 91% yield)

Workup

  1. customso obtained
  2. washThe organic layer was washed three times with water
  3. dry with materialonce with brine, dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe solid so obtained
  6. filtrationfiltered (79 mg, 91% yield)

Sources & evidence

ORD record
ord-3b964343fa184b3a8e9be5902dfbd1ec
Source dataset
uspto-grants-2014_07
Patent number
US08791265B2

Reaction notes

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