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 1772434Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772434
[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-0da9591fba434a61a6be326c81884eaa
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249133B2

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