Epichlorohydrin → 9-Methoxy-6-[4-(oxiran-2-ylmethyl)piperazin-1-yl]-11h-indeno[1,2-c]quinolin-11-one

HRID 1170880노트

반응식

HRID 1170880 반응식
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C:8]3[C:9]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)=[N:10][C:11]4[C:16]([C:7]=3[C:6](=[O:26])[C:5]=2[CH:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4.[H-].[Na+].[CH2:29]([CH:31]1[O:33][CH2:32]1)Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]2[C:8]3[C:9]([N:17]4[CH2:22][CH2:21][N:20]([CH2:29][CH:31]5[CH2:32][O:33]5)[CH2:19][CH2:18]4)=[N:10][C:11]4[C:16]([C:7]=3[C:6](=[O:26])[C:5]=2[CH:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4

참가 물질

5

반응물 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 242059869-Methoxy-6-(piperazin-1-yl)-11H-indeno[1,2-c]quinolin-11-one

생성물 1

HCID 875667359-Methoxy-6-[4-(oxiran-2-ylmethyl)piperazin-1-yl]-11h-indeno[1,2-c]quinolin-11-one수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 5x (0.35 g, 1 mmol, obtained from the above Synthesis Example 12) in dry DMF (20 mL) was added NaH (60% in oil, 2.64 g, 66.0 mmol) at 0° C. for 1 hr. After stirring at room temperature for 8 hrs, epichlorohydrin (0.92 g, 10 mmol) was added and stirred for a further 1 hr. The reaction mixture was partitioned between H2O and CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The resultant residue was purified by column chromatography (MeOH/CH2Cl2=1:10) to give the title compound 5kkk (0.33 g, 84% yield).

후처리

  1. stirringstirred for a further 1 hr
  2. customThe reaction mixture was partitioned between H2O and CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe resultant residue was purified by column chromatography (MeOH/CH2Cl2=1:10)

출처 및 근거

ORD 기록
ord-3e69b72f9415437f8fe2790b15f26159
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829567B2

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