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Trimethyl orthovalerate → 7-benzyloxy-2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline

HRID 2383104
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HRID 2383104 반응식
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([NH:31][CH2:32][CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:25]([NH2:30])[CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:31]([CH2:32][CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:1]([CH2:2][CH2:3][CH2:4][CH3:5])=[N:30][C:25]=3[CH:26]=[N:27][C:28]=2[CH:29]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

3

반응물 2

HCID 83755Trimethyl orthovalerateHCID 670509287-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine

생성물 1

HCID 670509737-benzyloxy-2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline수율 84%

실험 절차

Under a nitrogen atmosphere, trimethyl orthovalerate (2.7 mL, 16 mmol) was added dropwise to a solution of 7-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine (3.0 g, 7.8 mmol), prepared as described in Parts A and B of Example 46, in xylenes (30 mL), and the reaction was heated at reflux for 24 hours. The reaction mixture was allowed to cool to ambient temperature; a precipitate formed, which was isolated by filtration, washed with hexanes, and dried for two hours in a vacuum oven to provide 2.96 g of 7-benzyloxy-2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline.

후처리

  1. custom
prepared
  • temperaturethe reaction was heated
  • temperatureat reflux for 24 hours
  • customa precipitate formed
  • customwhich was isolated by filtration
  • washwashed with hexanes
  • customdried for two hours in a vacuum oven
  • 출처 및 근거

    ORD 기록
    ord-4286c457b9364ab5aa216a2c58984b13
    출처 데이터셋
    uspto-grants-2012_09
    DOI
    10.6084/m9.figshare.5104873.v1
    특허 번호
    US08263594B2

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