Hydrochloric Acid → HCID 178442246, Verbindung

HRID 216418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216418
Cl.[F:2][C:3]([F:35])([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=2)=[CH:24][CH:23]=1)[C:4]([C:6]1[N:7](S(N(C)C)(=O)=O)[CH:8]=[C:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[N:10]=1)=[O:5].C[OH:37]>>[CH3:14][C:12]([CH3:13])([CH3:15])[CH2:11][C:9]1[N:10]=[C:6]([C:4]([OH:5])([OH:37])[C:3]([F:2])([F:35])[C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=3)=[CH:26][CH:27]=2)[NH:7][CH:8]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 686681282-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Produkt 1

HCID 178442246HCID 178442246, Verbindung

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Hydrogen chloride (4 M in 1,4-dioxane) (1 mL, 4 mmol) was added to an ambient temperature solution of 2-{difluoro[4-(5-fluoropyridin-2-yl)phenyl]acetyl}-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (20 mg, 0.04 mmol) in methanol (2 mL). After stirring at 70° C. for 1 h, volatiles were removed. The residue was partitioned between ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded the title compound. LCMS: 406 (M+H).

Aufarbeitung

  1. customvolatiles were removed
  2. customThe residue was partitioned between ethyl acetate and 10% aqueous sodium hydroxide
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8ebdd6c9ad4143af969f5a02a1247eb9
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193228B2

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