Potassium Carbonate → 2-[4-(4-chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide

HRID 660964Notes

Reaction equation

HRID 660964 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:30])[N:11]([CH2:13][C:14]([NH:16][C:17]([CH3:29])([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[CH3:18])=[O:15])[CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:37][C:38]([F:43])([F:42])[CH:39]1[O:41][CH2:40]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:40][CH:39]([OH:41])[C:38]([F:43])([F:42])[F:37])[C:10](=[O:30])[N:11]([CH2:13][C:14]([NH:16][C:17]([CH3:18])([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:26])[F:28])[CH:20]=3)[CH3:29])=[O:15])[CH:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 5207692-(Trifluoromethyl)oxiraneHCID 58012169HCID 58012169, compound

Product 1

HCID 580121122-[4-(4-chlorophenyl)-2-oxo-3-(3,3,3-trifluoro-2-hydroxypropyl)-2,3-dihydro-1H-imidazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

174 mg (0.397 mmol) of 2-[4-(4-chlorophenyl)-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-N-{1-methyl-1-[3-(trifluoromethyl)phenyl]ethyl}-acetamide from Example 234A, 12.8 mg (0.04 mmol) of tetra-n-butylammonium bromide and 37.5 mg (0.199 mmol) of potassium carbonate are placed in 0.45 ml of DMF and treated with 49.0 mg (0.437 mmol) of 1,1,1-trifluoro-2,3-epoxypropane. This is stirred for 1 hr at 130° C. The suspension is diluted with 5 ml of ethyl acetate and washed twice with 5 ml of water each time. The organic phase is dried over sodium sulphate and filtered. After evaporation the crude product is purified by preparative HPLC [Method 10]. 48 mg (22% of theory) of the target compound are obtained.

Workup

  1. washwashed twice with 5 ml of water each time
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. customAfter evaporation the crude product
  5. customis purified by preparative HPLC [Method 10]
  6. custom48 mg (22% of theory) of the target compound are obtained

Sources & evidence

ORD record
ord-f52dec89510e4ad69145ac618d2d5ddf
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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