Dimethylformamide → 5-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]-N-propylpentanamide

Participants

Reaction Steps

5-[[1-[1-(3,4-Dimethoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic acid (197 mg, 0.35 mmol) prepared in Example 95 was dissolved in THF (10 ml), to which oxalyl chloride (0.079 ml, 1.05 mmol) and DMF (0.1 ml) were then added on ice and stirred at room temperature for 1 hour. After the reaction mixture was concentrated, the residue was dissolved in pyridine (10 ml) on ice and propylamine (62 mg, 1.05 mmol) was added thereto, followed by stirring at room temperature for 16 hours. After the reaction mixture was diluted with ethyl acetate, washed with water, dried and concentrated, the residue was applied to silica gel column chromatography (developing solvent: ethyl acetate/hexane=4/1) to give the titled compound (51 mg, yield: 24%) as a colorless oil. (cis:trans=1:2.8)

Provenance & Evidence