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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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
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HRID 2411886 반응식
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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9353aa67e8b34970b2867ee077a1ed32
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08816079B2

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