Sodium Hydroxide → 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

HRID 1062715Notes

Reaction equation

HRID 1062715 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([N:20](S(C2C=CC(C(C)(C)C)=CC=2)(=O)=O)[S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[N:10]([CH3:47])[N:9]=1)(=O)C.[OH-].[Na+]>C(O)C>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([S:21]([NH:20][C:11]2[N:10]([CH3:47])[N:9]=[C:8]([O:7][CH2:6][CH2:5][OH:4])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:22])=[O:23])=[CH:29][CH:28]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 222819162-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

Product 1

HCID 222820434-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamideYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 4) (80 mg) in ethanol (20 ml) at room temperature was added 2M sodium hydroxide (2 ml) and the mixture was stirred for 16 hrs. The mixture was reduced in volume to 10 ml by rotary evaporation, diluted with water (50 ml) and extracted with ethyl acetate (2×50 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10 g) eluted with dichloromethane to yield the title compound as a white solid (25 mg).

Workup

  1. customThe mixture was reduced in volume to 10 ml by rotary evaporation
  2. additiondiluted with water (50 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. dry with materialThe organic fraction was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica (10 g)
  8. washeluted with dichloromethane

Sources & evidence

ORD record
ord-7f2f859fd8ef43299485ae3bc799d806
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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