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

HRID 585386

반응식

HRID 585386 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bb9fb9a1f0864d2cb6d469f5056abb98
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930104B2

연결된 노트

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