Water → 3-[2-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-oxoethyl]-5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione

HRID 1038554Notes

Reaction equation

HRID 1038554 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH3:17])[NH:14][C:13](=[O:15])[NH:12][C:11]3=[O:16])=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([O:31][C:32]([C:41]1[N:46]=[CH:45][C:44]([N:47]2[CH2:52][CH2:51][N:50]([C:53](=[O:56])[CH2:54]Br)[CH2:49][CH2:48]2)=[C:43]([CH2:57][CH2:58][CH3:59])[CH:42]=1)([C:37]([F:40])([F:39])[F:38])[C:33]([F:36])([F:35])[F:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O>[CH2:24]([O:31][C:32]([C:41]1[N:46]=[CH:45][C:44]([N:47]2[CH2:52][CH2:51][N:50]([C:53](=[O:56])[CH2:54][N:12]3[C:11](=[O:16])[C:10]([C:8]4[CH:7]=[CH:6][C:5]5[O:1][CH2:2][CH2:3][C:4]=5[CH:9]=4)([CH3:17])[NH:14][C:13]3=[O:15])[CH2:49][CH2:48]2)=[C:43]([CH2:57][CH2:58][CH3:59])[CH:42]=1)([C:33]([F:34])([F:35])[F:36])[C:37]([F:38])([F:40])[F:39])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 665984355-(2,3-Dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dioneHCID 866471991-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-bromoethanone

Product 1

HCID 866472003-[2-(4-{6-[2-(Benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-oxoethyl]-5-(2,3-dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dioneYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2,3-Dihydrobenzofuran-5-yl)-5-methylimidazolidine-2,4-dione (5.6 mg, 0.0240 mmol) was dissolved in N,N-dimethylformamide (500 μL), and potassium carbonate (7.5 mg, 0.0545 mmol) was added under ice-cold conditions. The mixture was stirred at room temperature for 5 minutes. Then, under ice-cold conditions, 1-(4-{6-[2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl]-4-propylpyridin-3-yl}piperazin-1-yl)-2-bromoethanone (13 mg, 0.0218 mmol) was added and stirred at room temperature for 18 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 (13 mg (yield 78%)) was obtained as a yellow oil.

Workup

  1. stirringstirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-51d96834ffbc4d67a68f1a75cae3bf57
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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