1,2-Ethanediamine, N1,N1,N2-trimethyl- → 6-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(2-methoxyphenylaminomethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Participants

Reaction Steps

A mixture of 6-(4-hydroxy-2-methoxyphenyl)-5-[N-(2-methoxyphenyl)-N-(9-fluorenylmethoxycarbonyl)aminomethyl]-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 5, 25.0 mg, 0.0383 mmol), 1,1′-carbonyldiimidazole (62.0 mg, 0.382 mmol) and 4-dimethylaminopyridine (0.5 mg, 0.004 mmol) was dissolved in anhydrous tetrahydrofuran (1 mL), and then the solution was stirred at room temperature for 4.5 hours. N,N,N′-trimethylethylenediamine (39.2 mg, 0.383 mmol) was added thereto, and then the mixture was stirred at 60° C. for 2 hours. The reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate). The obtained colorless amorphous product was dissolved in N,N-dimethylformamide (1 mL), and then piperidine (50 μL) was added thereto. After the reaction mixture was stirred at room temperature for 15 minutes, it was diluted with ethyl acetate (20 mL). The mixture was washed with water (15 mL) and saturated brine (15 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound mg) as a colorless amorphous product. (Yield 47%)

Provenance & Evidence