Potassium Carbonate → 5-chloro-4-[4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-2-fluoro-N-pyrimidin-4-ylbenzenesulfonamide

HRID 1401925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1401925
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:22])=[C:6]([S:8]([N:11](COCC)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])[CH:7]=1.ClC1C(F)=CC(F)=C(S(/N=C2/N=CN(COCC)C=C/2)(=O)=O)C=1.[Cl:47][C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([C:55]2[N:59]([CH3:60])[N:58]=[CH:57][CH:56]=2)[CH:49]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([O:54][C:51]2[CH:52]=[CH:53][C:48]([Cl:47])=[CH:49][C:50]=2[C:55]2[N:59]([CH3:60])[N:58]=[CH:57][CH:56]=2)=[CH:4][C:5]([F:22])=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)(=[O:9])=[O:10])[CH:7]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 59436509(NE)-5-chloro-N-[1-(ethoxymethyl)pyrimidin-4-ylidene]-2,4-difluorobenzenesulfonamide2×HCID 594366195-chloro-N-(ethoxymethyl)-2,4-difluoro-N-pyrimidin-4-ylbenzenesulfonamideHCID 1355532144-Chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol

Produkt 1

HCID 468415015-chloro-4-[4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]-2-fluoro-N-pyrimidin-4-ylbenzenesulfonamideAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 5-chloro-N-(ethoxymethyl)-2,4-difluoro-N-pyrimidin-4-ylbenzenesulfonamide and 5-chloro-N-[(4E)-1-(ethoxymethyl)pyrimidin-4(1H)-ylidene]-2,4-difluorobenzenesulfonamide and 5-chloro-N-[(4E)-1-(ethoxymethyl)pyrimidin-4(1H)-ylidene]-2,4-difluorobenzenesulfonamide (Preparation 719) used as a mixture of three regioisomers, (64 mg, 0.18 mmol), 4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenol (Preparation 89) (37 mg, 0.18 mmol) and potassium carbonate (37 mg, 0.26 mmol) in dimethyl sulfoxide (1 mL) was stirred at room temperature for 19 hours then diluted with ethyl acetate (30 mL), washed with 1M aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was taken up in trifluoroacetic acid (1 mL) and stirred for 3 hours then concentrated in vacuo. The residue was purified by reverse phase HPLC to give 29 mg (27%) of the desired product as a white solid.

Aufarbeitung

  1. washwashed with 1M aqueous sodium hydroxide, water, saturated aqueous sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. stirringstirred for 3 hours
  5. concentrationthen concentrated in vacuo
  6. customThe residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-df57dcd926d64faf94ad08ffc60d40fe
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907101B2

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