Methanol → 8-(4-benzyloxy-phenyl)-2-methyl-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid (2-methoxy-ethyl)-phenyl-amide

HRID 362560노트

반응식

HRID 362560 반응식
[CH3:1][O:2][CH2:3][CH2:4][N:5]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:6]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[C:11](=[O:21])[N:12]2[C:17]=1[C:16]1[S:18][CH:19]=[CH:20][C:15]=1[CH:14]=[CH:13]2)=[O:7].[CH2:42]([Li])CCC.CI.CO>O1CCCC1.CCCCCC>[CH3:1][O:2][CH2:3][CH2:4][N:5]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:6]([C:8]1[CH:9]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[C:11](=[O:21])[N:12]2[C:17]=1[C:16]1[S:18][C:19]([CH3:42])=[CH:20][C:15]=1[CH:14]=[CH:13]2)=[O:7]

참가 물질

7

반응물 4

HCID 887MethanolHCID 6328Methyl iodideHCID 566362588-(4-Benzyloxy-phenyl)-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid (2-methoxy-ethyl)-phenyl-amideHCID 178418339Butyllithium

생성물 1

HCID 566389288-(4-benzyloxy-phenyl)-2-methyl-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid (2-methoxy-ethyl)-phenyl-amide수율 35%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-20 °C

실험 절차

500 mg (0.89 mmol) of 8-(4-benzyloxy-phenyl)-7-oxo-7H-thieno[2,3-a]-quinolizine-10-carboxylic acid (2-methoxy-ethyl)-phenyl-amide in 50 ml of tetrahydrofuran were lithiated at -70° C. with 1.1 ml of 1.6N n-butyllithium solution in hexane. After stirring at -70° C. for 1 hour 0.17 ml (2.68 mmol) of methyl iodide was added thereto and the mixture was left to warm to -20° C. during 5 hours. Then, 20 ml of methanol were added thereto, the mixture was left to warm to room temperature, treated with 40 ml of aqueous buffer solution pH 4 and extracted with dichloromethane. Drying with sodium sulphate, evaporation of the solvent and chromatography over silica gel with ethyl acetate/hexane 1:1 gave 0.18 g (35%) of 8-(4-benzyloxy-phenyl)-2-methyl-7-oxo-7H-thieno[2,3-a]quinolizine-10-carboxylic acid (2-methoxyethyl)-phenyl-amide as a yellow foam.

후처리

  1. additionwas added
  2. waitthe mixture was left
  3. waitthe mixture was left
  4. temperatureto warm to room temperature
  5. extractionextracted with dichloromethane
  6. dry with materialDrying with sodium sulphate, evaporation of the solvent and chromatography over silica gel with ethyl acetate/hexane 1:1

출처 및 근거

ORD 기록
ord-6197082d4e1e458599b8a4408035f4ec
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05869500

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