Potassium Carbonate → 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-phenyl-1H-pyrazol-5-yl]-N-[(2-methoxyethoxy)methyl]benzenesulfonamide

HRID 1368644Notes

Reaction equation

HRID 1368644 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([N:19]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])[N:10]([CH3:39])[N:9]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([S:26]([N:19]([C:11]2[N:10]([CH3:39])[N:9]=[C:8]([O:7][CH2:6][CH2:5][OH:4])[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])(=[O:28])=[O:27])=[CH:30][CH:31]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 222820392-[(5-{{[4-(tert-butyl)phenyl]sulfonyl}[(2-methoxyethoxy)methyl]amino}-1-methyl-4-phenyl-1H-pyrazol-3-yl)oxy]ethyl acetate

Product 1

HCID 222820064-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-phenyl-1H-pyrazol-5-yl]-N-[(2-methoxyethoxy)methyl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 2-[(5-{{[4-(tert-butyl)phenyl]sulfonyl}[(2-methoxyethoxy)methyl]amino}-1-methyl-4-phenyl-1H-pyrazol-3-yl)oxy]ethyl acetate (Preparation 16) (1.112 g) in solution in methanol (100 ml) was added a solution of potassium carbonate (890 mg) in water (25 ml), at room temperature. The reaction was stirred at room temperature for 1.5 hours, and then overnight. The reaction was stripped down and the residue partitioned between dichloromethane (20 ml) and water (20 ml). The aqueous layer was extracted with dichloromethane (10 ml). The organics were combined and back-washed with brine (10 ml). The solution was dried on magnesium sulfate, filtered and concentrated under reduced pressure to yield the desired product as an off white solid (528 mg)

Workup

  1. customat room temperature
  2. customovernight
  3. customthe residue partitioned between dichloromethane (20 ml) and water (20 ml)
  4. extractionThe aqueous layer was extracted with dichloromethane (10 ml)
  5. washback-washed with brine (10 ml)
  6. customThe solution was dried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-326ad198845b4d4da4d37ad517ed0299
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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