Dichloromethane → 5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-N-methylpentanamide

HRID 585386

反応式

HRID 585386 の反応式
[CH:1]1[C:13]2[N:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:24](=[O:35])[C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)[CH:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40](O)=[O:41])[CH2:15]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.ClCCl.S(Cl)(Cl)=O.[CH3:50][NH2:51].CO>CN(C)C=O>[CH:10]1[C:11]2[N:12]([CH:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([C:24](=[O:35])[C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=4)[CH:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([NH:51][CH3:50])=[O:41])[CH2:15]3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 223392535-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]pentanoic acidHCID 57454252Monomethylamine methanol

生成物 1

HCID 223393555-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-N-methylpentanamide収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

5-[4-(9H-9-Carbazolyl)-1-(3,4-dimethoxybenzoyl)-1,2,3,4-tetrahydro-2-quinolinyl]-pentanoic acid (0.12 g, 0.21 mmol) prepared in Example 128 was mixed with dichloromethane (5 ml), N,N-dimethylformamide (100 μl) and thionyl chloride (24 μl). The resulting mixture was stirred at 50° C. for 30 minutes and then cooled on ice, followed by addition of a 40% methylamine/methanol solution (1 ml), and stirring was continued at room temperature for an additional 4 hours. The reaction mixture was partitioned between ethyl acetate and saturated brine, washed and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/4) to give the titled compound (0.10 g, yield: 83%) as a white crystal (cis:trans=4:1).

後処理

  1. temperaturecooled on ice
  2. stirringstirring
  3. waitwas continued at room temperature for an additional 4 hours
  4. customThe reaction mixture was partitioned between ethyl acetate and saturated brine
  5. washwashed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter distilling off the solvent

出典と根拠

ORDレコード
ord-bb9fb9a1f0864d2cb6d469f5056abb98
出典データセット
uspto-grants-2005_08
特許番号
US06930104B2

関連ノート

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