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

HRID 1062720

Reaktionsgleichung

Reaktionsgleichung von HRID 1062720
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]([NH2:20])[N:10]([CH3:21])[N:9]=1)(=O)C.[H-].[Na+].[C:24]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1)([CH2:27][CH3:28])([CH3:26])[CH3:25]>CC(N(C)C)=O.O>[OH: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]([NH:20][S:35]([C:32]2[CH:33]=[CH:34][C:29]([C:24]([CH2:27][CH3:28])([CH3:25])[CH3:26])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[N:10]([CH3:21])[N:9]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 222819764-(2-Methylbutan-2-yl)benzene-1-sulfonyl chlorideHCID 222820022-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

Produkt 1

HCID 22281988N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]4-(tert-pentyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To 2-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (Preparation 5) (1.0 g) in dimethylacetamide (10 ml) at 0° C. under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 415 mg) followed by 4-tert-amylbenzenesulphonyl chloride and (938 mg), the mixture was stirred for 2 hrs. The reaction was diluted with water (50 ml) and extracted with dichloromethane (5×30 ml). The crude mixture was dissolved in ethanol (50 ml) and sodium hydroxide (2N, 5 ml) was added, the mixture was stirred at room temperature for 48 hrs and then neutralised to pH 7 by addition of hydrochloric acid (2N) and extracted with dichloromethane (2×50 ml). The organic fractions were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 10 g) eluted with ethyl acetate:hexane (1:1) to yield the title compound as a white solid (290 mg).

Aufarbeitung

  1. extractionextracted with dichloromethane (5×30 ml)
  2. dissolutionThe crude mixture was dissolved in ethanol (50 ml)
  3. additionsodium hydroxide (2N, 5 ml) was added
  4. stirringthe mixture was stirred at room temperature for 48 hrs
  5. additionneutralised to pH 7 by addition of hydrochloric acid (2N)
  6. extractionextracted with dichloromethane (2×50 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (silica, 10 g)
  11. washeluted with ethyl acetate:hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-07fcd6a8d82b409b89b17cca2b21e813
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962923B2

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