Dichloromethane → HCID 68109717, compound

Participants

Reaction Steps

N-Boc-glycine (84.7 mg, 0.48 mmol) and EDCI HCl (92.6 mg, 0.48 mmol) were added to 6 mL of methylene chloride solution of (2-aminophenyl)-quinolin-3-yl-methanone (0.12 g, 0.48 mmol) under a nitrogen atmosphere at 0° C., followed by bringing back to room temperature and stirring for 45 hours. The resulting reaction solution was poured into 10 mL of ethyl acetate and 50 mL of water, and the aqueous layer was extracted with 100 mL of ethyl acetate, followed by washing the combined organic layer with 50 mL of brine and drying with magnesium sulfate. After filtering and concentrating, the resulting residue was purified by silica gel column chromatography to obtain {[2-(quinoline-3-carbonyl)-phenylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (0.07 g, yield: 36%), which was slightly yellow amorphous. Moreover, 1 mL of trifluoroacetic acid was added to this compound, followed by stirring at room temperature for 16 hours. The resulting reaction solution was poured into a mixture of 10 mL of ethyl acetate, 50 mL of saturated sodium bicarbonate water and 50 mL of water, the aqueous layer was extracted with 100 mL of ethyl acetate, and the combined organic layer was washed with 50 mL of brine, followed by extracting with magnesium sulfate. After filtering and concentrating, the resulting residue was dissolved in 10 mL of ethanol, and 0.5 g of acetic acid was added to the resulting solution. The solution was heated to reflux, and maintained for 30 minutes. The reaction solution was poured into a mixture of 100 mL of ethyl acetate, 50 mL of saturated sodium bicarbonate water and 50 mL of water, and the aqueous layer was extracted with 100 mL of ethyl acetate. The combined organic layer was washed with 50 mL of brine, followed by drying with magnesium sulfate. After filtering and concentrating, the resulting residue was purified by silica gel column chromatography to obtain the target compound (0.03 g, yield: 61%), which was slightly yellow amorphous.

Provenance & Evidence