Propylamine → HCID 22339194, compound

Participants

Reaction Steps

5-[[1-[1-(3,4-Dimethylbenzoyl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]-1,2,3,4-tetrahydro-6-quinolinyl]oxy]pentanoic acid (0.20 g, 0.37 mmol) prepared in Example 164 and 1-hydroxybenzotriazole (50 mg, 0.37 mmol) were dissolved in N,N-dimethylformamide (3 ml). To this solution, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (92 mg, 0.48 mmol) was added and the resulting mixture was stirred at room temperature for 10 minutes. After addition of propylamine (91 μl), the mixture was stirred at room temperature for an additional 15 hours. Aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted with ethyl acetate. The extracted solution was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 4:1) to give the titled compound (0.14 g, yield: 68%) as an amorphous powder. (cis:trans=3:2)

Provenance & Evidence