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

HRID 1170880ノート

反応式

HRID 1170880 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3e69b72f9415437f8fe2790b15f26159
出典データセット
uspto-grants-2010_11
特許番号
US07829567B2

反応ノート

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