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

HRID 1368641Notes

Reaction equation

HRID 1368641 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]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[C:11]([N:23]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[N:10]([CH3:43])[N:9]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:39]([C:36]1[CH:35]=[CH:34][C:33]([S:30]([N:23]([C:11]2[N:10]([CH3:43])[N:9]=[C:8]([O:7][CH2:6][CH2:5][OH:4])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])(=[O:31])=[O:32])=[CH:38][CH:37]=1)([CH3:42])([CH3:40])[CH3:41]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 222819502-({5-{{[4-(tert-butyl)phenyl]sulfonyl}[(2-methoxyethoxy)methyl]amino}-1-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)ethyl Acetate

Product 1

HCID 222819664-(tert-butyl)-N-{3-(2-hydroxyethoxy)-1-methyl-4-[4-(trifluoromethyl)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-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}oxy)ethyl acetate (Preparation 13) (200 mg) in methanol (20 ml) was added a solution of potassium carbonate (90 mg) in water (5 ml), at room temperature. The reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was stripped down and the residue partitioned between ethyl acetate (15 ml) and water (15 ml). The aqueous layer was extracted with ethyl acetate (2×15 ml). The combined organics were back-washed with brine (15 ml). The solution was dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the desired product as an off white solid (170 mg).

Workup

  1. customat room temperature
  2. customthe residue partitioned between ethyl acetate (15 ml) and water (15 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×15 ml)
  4. washThe combined organics were back-washed with brine (15 ml)
  5. dry with materialThe solution was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ea6cbf1b6e64d45a7968dc54dd7b1da
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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