Cesium carbonate → HCID 90405153, compound

HRID 573833Notes

Reaction equation

HRID 573833 reaction equation
[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]

Participants

10

Reactant 6

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 517045Sodium AcetateHCID 2759507(2-(Propan-2-yl)phenyl)thioureaHCID 3034336ThiobiuretHCID 90404087HCID 90404087, compound

Product 1

HCID 90405153HCID 90405153, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-a2e0acf7dcf5425cbc4e9078be621e16
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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