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Dimethyl Sulfoxide → HCID 86657924, Verbindung

HRID 1186303
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1186303
Cl[C:2]1[C:11]([O:12][CH:13]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:14]([F:17])([F:16])[F:15])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CS(C)=O.[F:28][C:29]([F:35])([F:34])[S:30]([NH2:33])(=[O:32])=[O:31].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[F:28][C:29]([F:35])([F:34])[S:30]([NH:33][C:2]1[C:11]([O:12][CH:13]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:14]([F:17])([F:16])[F:15])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)(=[O:32])=[O:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 79001TrifluoromethylsulfonamideHCID 86657923HCID 86657923, Verbindung

Produkt 1

HCID 86657924HCID 86657924, VerbindungAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Versuchsvorschrift

According to Example 132, by use of 2-chloro-3-[2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy]-quinoxaline (Compound BJ) (70 mg, 0.21 mmol), dimethyl sulfoxide (2 mL), trifluoromethanesulfonamide (31 mg, 0.21 mmol) and potassium carbonate (28 mg, 0.21 mmol), the mixture was stirred and reacted at 150° C. for 1.5 hours. The reaction mixture was allowed to cool down to room temperature, a 1% aqueous acetic acid solution was added thereto, and extraction with ethyl acetate was performed. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 20/1). Further, slurry purification was performed using isopropyl ether, to give 1,1,1-trifluoro-N-{3-[2,2,2-trifluoro-1-(pyridin-3-yl)-ethoxy]quinoxalin-2-yl}methanesulfonamide (Compound 149) (13 mg, 14%).

Aufarbeitung

  1. customreacted at 150° C. for 1.5 hours
  2. extractionextraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 20/1)
  7. customFurther, slurry purification

Quellen und Nachweise

ORD-Eintrag
ord-b1ddb4e7b8434c85995a33bab106149f
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673908B2

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