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 1038554ノート

反応式

HRID 1038554 の反応式
[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

参加物

6

反応物 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

生成物 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-dione収率 81.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-51d96834ffbc4d67a68f1a75cae3bf57
出典データセット
uspto-grants-2013_10
特許番号
US08551985B2

反応ノート

読み込み中…