Water → HCID 86647192, compound

HRID 1038544Notes

Reaction equation

HRID 1038544 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][N:10]=2)[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:32][C:33]([C:42]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][N:51]([C:54](=[O:57])[CH2:55]Br)[CH2:50][CH2:49]2)=[C:44]([CH:58]=[CH:59][CH3:60])[CH:43]=1)([C:38]([F:41])([F:40])[F:39])[C:34]([F:37])([F:36])[F:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C)C=O>[CH2:25]([O:32][C:33]([C:42]1[CH:47]=[CH:46][C:45]([N:48]2[CH2:53][CH2:52][N:51]([C:54](=[O:57])[CH2:55][N:4]3[C:3](=[O:8])[C:2]([C:9]4[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:11][N:10]=4)([CH3:1])[NH:6][C:5]3=[O:7])[CH2:50][CH2:49]2)=[C:44](/[CH:58]=[CH:59]\[CH3:60])[CH:43]=1)([C:34]([F:35])([F:36])[F:37])[C:38]([F:39])([F:40])[F:41])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 665980545-[5-(1-Methylethoxy)pyridin-2-yl]-5-methylimidazolidine-2,4-dioneHCID 866471931-(4-{4-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-(prop-1-en-1-yl)phenyl}piperazin-1-yl)-2-bromoethanone

Product 1

HCID 86647192HCID 86647192, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Methyl-5-[5-(1-methylethoxy)pyridin-2-yl]imidazolidine-2,4-dione (7.7 mg, 0.0309 mmol) was dissolved in N,N-dimethylformamide (2.8 mL), added potassium carbonate (9.3 mg, 0.0674 mmol) under ice-cold conditions, and the mixture was stirred at room temperature for 5 minutes. Then, under ice-cold conditions, 1-(4-{4-[2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-(prop-1-en-1-yl)phenyl}piperazin-1-yl)-2-bromoethanone (16 mg, 0.0281 mmol) was added, and stirred at room temperature overnight. Then, the mixture was stirred at 60° C. for 10 hours. Under ice-cold conditions, the reaction solution was added water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone), and the title compound (17 mg (yield 80%)) was obtained as a yellow oil.

Workup

  1. stirringstirred at room temperature overnight
  2. stirringThen, the mixture was stirred at 60° C. for 10 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-0049d8ab13394d6fbb521a77424cbdf4
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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