Cesium carbonate → HCID 58011753, compound

HRID 660948Notes

Reaction equation

HRID 660948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][C:18]([CH3:30])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH3:19])=[O:16])[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:37][C:38]([F:43])([F:42])[CH:39]1[O:41][CH2:40]1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:40][CH:39]([OH:41])[C:38]([F:43])([F:42])[F:37])[C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][C:18]([CH3:30])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)[CH3:19])=[O:16])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5207692-(Trifluoromethyl)oxiraneHCID 136199107HCID 136199107, compound

Product 1

HCID 58011753HCID 58011753, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

3.61 g (8.23 mmol) of 2-[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 241A are dissolved in 20 ml of DMF with 3.75 g (11.52 mmol) of caesium carbonate and treated with 2.22 g (11.52 mmol) of 1,1,1-trifluoro-2,3-epoxypropane. This is stirred for 2.5 hrs at 75° C. The suspension is then diluted with 30 ml of ethyl acetate and washed twice with 20 ml water each time. The organic phase is dried over sodium sulphate and filtered. After concentration, the crude product is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate first 5:1, then 1:1). 3.14 g (69% of theory) of the target compound are thus obtained.

Workup

  1. washwashed twice with 20 ml water each time
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationAfter concentration
  5. customthe crude product is purified by flash chromatography on silica gel (eluent
  6. custom3.14 g (69% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-b46fa390dc0d4e5fa52c4751ac5d1132
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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