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 1038554노트

반응식

HRID 1038554 반응식
[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

참가 물질

6

반응물 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

생성물 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-dione수율 81.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-51d96834ffbc4d67a68f1a75cae3bf57
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551985B2

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