Potassium Carbonate → 3-Cyano-N-(5-fluoro-1,3-thiazol-2-yl)-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}benzenesulfonamide

HRID 1619598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619598
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:12]=2[OH:13])=[CH:5][CH:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[C:26]([C:28]1[CH:29]=[C:30]([S:35]([NH:38][C:39]2[S:40][C:41]([F:44])=[CH:42][N:43]=2)(=[O:37])=[O:36])[CH:31]=[CH:32][C:33]=1F)#[N:27].[Cl-].[NH4+]>CN(C)C=O>[C:26]([C:28]1[CH:29]=[C:30]([S:35]([NH:38][C:39]2[S:40][C:41]([F:44])=[CH:42][N:43]=2)(=[O:37])=[O:36])[CH:31]=[CH:32][C:33]=1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][C:7]=1[C:6]1[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=1)#[N:27]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 580422733-cyano-4-fluoro-N-(5-fluoro-1,3-thiazol-2-yl)benzenesulfonamideHCID 1362008913-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol

Produkt 1

HCID 566009953-Cyano-N-(5-fluoro-1,3-thiazol-2-yl)-4-{[3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-yl]oxy}benzenesulfonamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol (Preparation 28, 188 mg, 0.75 mmol) and potassium carbonate (173 mg, 1.25 mmol) in N,N-dimethylformamide (2.5 mL) was added 3-cyano-4-fluoro-N-(5-fluoro-1,3-thiazol-2-yl)benzenesulfonamide (Preparation 34, 151 mg, 0.5 mmol) and the reaction mixture was stirred at 80° C. After stirring for 16 hours, the reaction mixture was cooled to room temperature. Saturated aqueous ammonium chloride (10 mL) was added to the reaction mixture and the mixture was extracted with dichloromethane (3×10 mL). The collected organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to obtain a crude residue. The residue was purified by silica gel column chromatography (40% ethyl acetate in dichloromethane elution) to afford the title compound as a white solid (127 mg, 48%).

Aufarbeitung

  1. stirringAfter stirring for 16 hours
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with dichloromethane (3×10 mL)
  4. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto obtain a crude residue
  8. customThe residue was purified by silica gel column chromatography (40% ethyl acetate in dichloromethane elution)

Quellen und Nachweise

ORD-Eintrag
ord-ad41f63f03c34b8696365bde3c553c1e
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

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