N,N'-Dimethylethylenediamine → 1-{5-Chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-3-methylimidazolidin-2-one

HRID 2411368ノート

反応式

HRID 2411368 の反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10].[CH3:25][N:26]1[CH2:30][CH2:29][NH:28][C:27]1=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+].CNCCNC>[Cu]I.O.O1CCOCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[O:10])=[C:2]([N:28]2[CH2:29][CH2:30][N:26]([CH3:25])[C:27]2=[O:31])[CH:7]=1

参加物

8

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 5676001-Methylimidazolidin-2-oneHCID 58484730(2-Bromo-4-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

生成物 1

HCID 584848021-{5-Chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-3-methylimidazolidin-2-one収率 38.6%

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

To a mixture of (2-bromo-4-chlorophenyl) [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (817 mg) described in Preparation Example 167, 1-methylimidazolidin-2-one (300 mg), cesium carbonate (1.30 g) and copper(I) iodide (191 mg) were added 1,4-dioxane (4 mL) and N,N′-dimethylethylenediamine (0.22 mL), and the mixture was stirred for 8 hr under refluxing. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The solvent was evaporated, and the residue was purified by column chromatography (ethyl acetate:methanol) to give the title compound (330 mg).

後処理

  1. temperatureunder refluxing
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography (ethyl acetate:methanol)

出典と根拠

ORDレコード
ord-f8f9fa35d3cb42b0913469084ffedb5e
出典データセット
uspto-grants-2014_08
特許番号
US08816079B2

反応ノート

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