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

HRID 2411368노트

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HRID 2411368 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f8f9fa35d3cb42b0913469084ffedb5e
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816079B2

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