3-(Difluoromethoxy)benzenesulfonyl chloride → 3-Difluoromethoxy-N-[2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-benzene sulfonamide

HRID 454873Notes

Reaction equation

HRID 454873 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[F:15][CH:16]([F:28])[O:17][C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>N1C=CC=CC=1>[F:28][CH:16]([F:15])[O:17][C:18]1[CH:19]=[C:20]([S:24]([NH:14][C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[CH:13]=2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 27782263-(Difluoromethoxy)benzenesulfonyl chlorideHCID 118391892-(4-Methylpiperazin-1-yl)pyridin-4-amine

Product 1

HCID 167557643-Difluoromethoxy-N-[2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-benzene sulfonamideYield 55.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 200 mg of 2-(4-methyl-piperazin-1-yl)-4-amino-pyridin (1.04 mmol) in 5 ml of pyridine 272 mg of (1.12 mmol) of 3-difluoromethoxybenzene sulfonylchloride (1.66 mmol) were added and the reaction mixture was stirred for 15 h at room temperature. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane. This mixture was washed with aqueous NaHCO3. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified via silica gel chromatography with ethyl dichloromethane/methanol (0-15%) as eluent, yielding 231 mg of the purified product.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThis mixture was washed with aqueous NaHCO3
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe crude product was purified via silica gel chromatography with ethyl dichloromethane/methanol (0-15%) as eluent

Sources & evidence

ORD record
ord-426556b680484ac58f88921740542288
Source dataset
uspto-grants-2013_07
Patent number
US08497273B2

Reaction notes

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