N,N'-二甲基乙二胺 → 1-{5-Chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}-3-methylimidazolidin-2-one

HRID 2411368笔记

反应方程式

HRID 2411368 反应方程式
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

参与物

8

反应物 4

HCID 8070N,N'-二甲基乙二胺HCID 10796碳酸氢铯HCID 5676001-甲基-2-咪唑啉酮HCID 58484730(2-Bromo-4-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

产物 1

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

试剂、催化剂与溶剂 3

HCID 24350碘化亚铜催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 312751,4-二氧六环溶剂

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-f8f9fa35d3cb42b0913469084ffedb5e
来源数据集
uspto-grants-2014_08
专利号
US08816079B2

反应笔记

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