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

HRID 378668Notes

Reaction equation

HRID 378668 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

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-methoxy-ethyl)-phenyl-amide as a yellow foam.

Workup

  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

Sources & evidence

ORD record
ord-3d978a759148437caa051707a83f2116
Source dataset
uspto-grants-2000_02
Patent number
US06030984

Reaction notes

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