Water → HCID 89962890, Verbindung

HRID 337907

Reaktionsgleichung

Reaktionsgleichung von HRID 337907
[F:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)[CH:5]=[C:4]([F:20])[C:3]=1[S:21]([NH2:24])(=[O:23])=[O:22].[F:25][C:26]1[N:31]=[C:30](F)[CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:20][C:4]1[CH:5]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)[CH:7]=[C:2]([F:1])[C:3]=1[S:21]([NH:24][C:28]1[CH:29]=[CH:30][N:31]=[C:26]([F:25])[N:27]=1)(=[O:23])=[O:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1377162,4-DifluoropyrimidineHCID 89962731HCID 89962731, Verbindung

Produkt 1

HCID 89962890HCID 89962890, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the 2,6-difluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamide (0.23 g, 0.65 mmol) prepared in Example 111c, 2,4-difluoropyrimidine (0.23 g, 1.96 mmol) and potassium carbonate (0.36 g, 2.61 mmol) in DMF (6.5 mL) was stirred at 120° C. for 3 hours. After allowing to cool, water (50 mL) was added to the reaction solution, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was washed twice with water (50 mL) and dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (ethyl acetate/methanol=6:1) to yield the title compound (150 mg, 51%) as a colorless amorphous solid.

Aufarbeitung

  1. temperatureto cool
  2. extractionfollowed by extraction with ethyl acetate (50 mL)
  3. washThe thus obtained organic layer was washed twice with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (ethyl acetate/methanol=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-dfd2049633c94755aa00dccbf896d9a1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889741B2

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