Cesium carbonate → (1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea

HRID 1772439Notes

Reaction equation

HRID 1772439 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)=[C:2]=[O:3].[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[NH:38][C:39]([NH2:41])=[S:40])([CH3:30])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:49][C:50](OC)=[O:51].C([O-])(=O)C.[Na+]>C(O)C.C(#N)C>[CH:28]([C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[N:38]1[C:50](=[O:51])[CH2:49][S:40]/[C:39]/1=[N:41]\[C:2]([NH:1][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:26])([F:25])[F:27])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)=[O:3])([CH3:30])[CH3:29]

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 517045Sodium AcetateHCID 893731681-(2-Isopropyl-5-methylphenyl)thioureaHCID 904044083-(4-(2-Isocyanatoethyl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 78319090(1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a 250 mL round bottomed flask was added acetonitrile (100 mL). 3-(4-(2-Isocyanatoethyl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (34a) (11.0 g, 29.4 mmol) was added in one portion. 1-(2-Isopropyl-5-methylphenyl)thiourea (6.73 g, 32.3 mmol) and cesium carbonate (9.57 g, 29.4 mmol) were added to the above solution. The reaction mixture was stirred at room temperature under nitrogen overnight. Ethanol (100 mL) was added to the mixture. Methyl 2-bromoacetate (8.99 g, 58.8 mmol) and sodium acetate (9.64 g, 118 mmol) were then added. The reaction mixture was stirred at 60° C. for 2 hours, forming an orange suspension. The reaction mixture was cooled and filtered through a filter paper, and the solids were washed with ethyl acetate (2×100 mL). The orange filtrate was concentrated. The solid residue was purified by flash column chromatography using 10-20% dichloromethane/B, where B=1:1 ethyl acetate/acetone, as eluent to afford the title compound as a slightly orange foam (8.60 g, 45%).

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 2 hours
  2. customforming an orange suspension
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through a filter paper
  5. washthe solids were washed with ethyl acetate (2×100 mL)
  6. concentrationThe orange filtrate was concentrated
  7. customThe solid residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-942b7ed97f6d4a6ba4d66e8818022062
Source dataset
uspto-grants-2016_02
Patent number
US09249133B2

Reaction notes

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