Cesium carbonate → HCID 58011780, compound

HRID 660963Notes

Reaction equation

HRID 660963 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[NH:21][C:20](=[O:22])[N:19]([CH2:23][C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=3)=[O:25])[N:18]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[C:6]([O:5][C:3](=[O:4])[CH2:2][N:21]1[C:20](=[O:22])[N:19]([CH2:23][C:24](=[O:25])[NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[N:18]=[C:17]1[C:14]1[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][CH:15]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 136199112HCID 136199112, compound

Product 1

HCID 58011780HCID 58011780, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

92.6 mg (0.475 mmol) of tert.-butyl bromoacetate are added to 150.0 mg of (0.365 mmol) 2-[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[3-(trifluoromethyl)phenylmethyl]-acetamide from Example 242A and 178.5 mg (0.548 mmol) of caesium carbonate in 5.0 ml of acetone and heated for 5 hrs under reflux. For the workup, the reaction mixture is concentrated after cooling, the residue is partitioned between water and ethyl acetate, the organic phase separated and the aqueous phase extracted several times more with ethyl acetate. The combined organic phases are concentrated and the residue purified by preparative HPLC [Method 12]. 139 mg (73% of theory) of the target compound are thus obtained.

Workup

  1. temperatureheated for 5 hrs
  2. temperatureunder reflux
  3. concentrationFor the workup, the reaction mixture is concentrated
  4. temperatureafter cooling
  5. customthe residue is partitioned between water and ethyl acetate
  6. customthe organic phase separated
  7. extractionthe aqueous phase extracted several times more with ethyl acetate
  8. concentrationThe combined organic phases are concentrated
  9. customthe residue purified by preparative HPLC [Method 12]
  10. custom139 mg (73% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-1342075c1ba7410680a0d3aae747fad6
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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