Potassium Hydroxide → 2-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

HRID 1062779Notes

Reaction equation

HRID 1062779 reaction equation
[C:1]([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]([NH2:20])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].[OH-:36].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[C:11]([N:20]([S:32]([C:29]2[CH:30]=[CH:31][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=2)(=[O:33])=[O:36])[S:32]([C:29]2[CH:30]=[CH:31][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:27][CH:28]=2)(=[O:34])=[O:33])[N:10]([CH3:21])[N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 222820022-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

Product 1

HCID 222819162-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetateYield 62.1%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 5) (100 mg) in dichloromethane (3 ml) at room temperature was added 4-tert-butylbenzenesulfonylchloride (88 mg), tetrabutylammonium hydrogen sulfate (14 mg) and potassium hydroxide (42 mg), the mixture was sonicated for 3 hrs. The reaction was diluted with water (10 ml) and extracted with ethyl acetate (10 ml). The organic fraction was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 10 g) eluted with dichloromethane to yield the title compound as a white solid (80 mg).

Workup

  1. customthe mixture was sonicated for 3 hrs
  2. extractionextracted with ethyl acetate (10 ml)
  3. dry with materialThe organic fraction was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica, 10 g)
  7. washeluted with dichloromethane

Sources & evidence

ORD record
ord-eda1723b72cf4d35878edb6f25c6a684
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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