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N,N'-Dimethylethylenediamine → 3-Benzyloxymethyl-1-{4-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-methylimidazolidine-2,4-dione

HRID 2411886
ノート
印刷プレビュー

反応式

HRID 2411886 の反応式
CNCCNC.Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH:29]4[CH2:31][CH2:30]4)=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])=[C:10]([F:32])[CH:9]=1.[CH2:33]([O:40][CH2:41][N:42]1[C:46](=[O:47])[CH:45]([CH3:48])[NH:44][C:43]1=[O:49])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I.O.O1CCOCC1>[CH2:33]([O:40][CH2:41][N:42]1[C:46](=[O:47])[CH:45]([CH3:48])[N:44]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[C:27]([CH3:28])=[CH:26][C:25]([CH:29]5[CH2:31][CH2:30]5)=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[O:15])=[C:10]([F:32])[CH:9]=2)[C:43]1=[O:49])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 58484842(4-Bromo-2-fluorophenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanoneHCID 712522743-Benzyloxymethyl-5-methylimidazolidine-2,4-dione

生成物 1

HCID 712520443-Benzyloxymethyl-1-{4-[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazine-1-carbonyl]-3-fluorophenyl}-5-methylimidazolidine-2,4-dione

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

1,4-Dioxane (12 mL) and N,N′-dimethylethylenediamine (86 μL) were added to a mixture of (4-bromo-2-fluorophenyl)[4-(5-cyclopropyl-3-methylpyridin-2-yl)piperazin-1-yl]methanone (325 mg) described in Preparation Example 121, 3-benzyloxymethyl-5-methylimidazolidine-2,4-dione (225 mg) described in Preparation Example 206, cesium carbonate (521 mg) and copper(I) iodide (76 mg), and the mixture was stirred with heating under reflux for 10 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title is compound (270 mg).

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 10 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)
  9. customto give the title

出典と根拠

ORDレコード
ord-9353aa67e8b34970b2867ee077a1ed32
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08816079B2

反応ノート

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