Cesium carbonate → (1Z)-1-[4-oxo-3-(2-propan-2-ylphenyl)-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea

HRID 573833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573833
[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22]C(N=[N+]=[N-])=O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH:45][C:46]([NH2:48])=[S:47])([CH3:38])[CH3:37].NC([NH:52][C:53](N)=[O:54])=S.[C:56]([O-])(=[O:58])[CH3:57].[Na+].BrCC(OC)=O>C(#N)C.C(O)C.C(OCC)(=O)C>[CH:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N:45]1[C:56](=[O:58])[CH2:57][S:47]/[C:46]/1=[N:48]\[C:53]([NH:52][CH2:22][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:29])([F:28])[F:1])=[CH:9][CH:8]=3)[N:11]=2)=[CH:16][CH:17]=1)=[O:54])([CH3:38])[CH3:37]

Komponenten

10

Edukt 6

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 517045Sodium AcetateHCID 2759507(2-(Propan-2-yl)phenyl)thioureaHCID 3034336ThiobiuretHCID 904040873-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propanoyl azide

Produkt 1

HCID 90405153(1Z)-1-[4-oxo-3-(2-propan-2-ylphenyl)-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]ureaAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propanoyl azide (C34) (0.24 g, 0.59 mmol) in acetonitrile (2.9 mL) was heated at 80° C. for 2 hours. The reaction was cooled and cesium carbonate (0.29 g, 0.88 mmol) and 1-(2-isopropylphenyl)thiourea (0.14 g, 0.70 mmol) were added. The reaction was stirred at room temperature overnight. LC/MS showed formation of the thiobiuret was complete. The reaction mixture was diluted with ethanol (2.9 mL) and sodium acetate (0.19 g, 2.4 mmol) and methyl 2-bromoacetate (0.12 mL, 1.2 mmol) were added. The solution was heated at 65° C. for 2 hours. The reaction was diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and loaded onto a Celite® cartridge with dichloromethane. Purification by flash column chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes, as eluent afforded the title compound as a tan oil (0.22 g, 62%).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. additionwere added
  3. temperatureThe solution was heated at 65° C. for 2 hours
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a2e0acf7dcf5425cbc4e9078be621e16
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029560B2

Notizen zur Reaktion

Wird geladen…