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

HRID 1062730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062730
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14](S(C2C=CC(C(C)(C)C)=CC=2)(=O)=O)[C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:16]=2[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:16]=2[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 222818924-(tert-butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl}-N-[3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

Produkt 1

HCID 222820054-(tert-butyl)-N-[3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamideAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 4-(tert-butyl)-N-{[4-(tert-butyl)phenyl]sulfonyl}-N-[3-[2-(4-fluorophenoxy)ethoxy]-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Preparation 25) (180 mg) in dioxan 5 ml) at room temperature was added 1N aqueous sodium hydroxide (5 ml) and the mixture was stirred and heated to 100° C. for 1.5 hrs. The reaction was partitioned between 2N aqueous hydrochloric acid (25 ml) and ethyl acetate (25 ml). The organic layer was separated, washed with water, then brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel (20 g), eluting with a solvent gradient of pentane:ethylacetate (19:1 changing to 7:3), to yield the title compound as a glass (106 mg).

Aufarbeitung

  1. customThe reaction was partitioned between 2N aqueous hydrochloric acid (25 ml) and ethyl acetate (25 ml)
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with a solvent gradient of pentane:ethylacetate (19:1 changing to 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-a3027765dd0f410a955ae63dff428801
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962923B2

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