Sodium Carbonate → 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxothiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

HRID 1372891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372891
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([CH3:37])[C:17]2[CH:18]=[N:19][C:20]([N:31]3[CH2:36][CH2:35]S[CH2:33][CH2:32]3)=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[CH3:30])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O[O:43][S:44]([O-:46])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].S([O-])(O)=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C:17]2[CH:18]=[N:19][C:20]([N:31]3[CH2:32][CH2:33][S:44](=[O:46])(=[O:43])[CH2:35][CH2:36]3)=[CH:21][C:22]=2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[CH3:30])[CH3:37])=[O:15])[CH:4]=[C:3]([C:2]([F:40])([F:41])[F:1])[CH:8]=1

Komponenten

7

Edukt 5

HCID 10340Sodium CarbonateHCID 10313463Potassium peroxymonosulphateHCID 22591451HCID 22591451, VerbindungHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 98307032-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxothiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2-(3,5-Bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide can be produced by suspending 2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-isobutyramide in methanol and treating it at room temperature with oxone™ (potassium peroxymonosulfate). The suspension is then stirred for about 16 hours at room temperature and cooled to about 0° C., followed by the dropwise addition of sodium hydrogen sulfite solution. After stirring at room temperature, the pH is adjusted to about 8.5 with saturated aqueous sodium carbonate. The methanol is then evaporated under reduced pressure, and the residue is extracted with dichloromethane. The organic phase is washed with half-saturated aqueous sodium chloride. The solvent is exchanged under reduced pressure in a rotary evaporator with isopropanol, and the volume reduced. The solution is cooled to room temperature under stirring and stirred further for about 1 hour. The precipitate formed is filtered off, washed with isopropanol, and dried under high vacuum to yield 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxothiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide as a white powder.

Aufarbeitung

  1. temperaturecooled to about 0° C.
  2. stirringAfter stirring at room temperature
  3. customThe methanol is then evaporated under reduced pressure
  4. extractionthe residue is extracted with dichloromethane
  5. washThe organic phase is washed with half-saturated aqueous sodium chloride
  6. customThe solvent is exchanged under reduced pressure in a rotary evaporator with isopropanol
  7. temperatureThe solution is cooled to room temperature
  8. stirringunder stirring
  9. stirringstirred further for about 1 hour
  10. customThe precipitate formed
  11. filtrationis filtered off
  12. washwashed with isopropanol
  13. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ceb2a621f4094090b20d4a002ca19d72
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160881B2

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