Acetonitrile → HCID 73347360, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask, was added 3-hydroxyquinoline-4-carboxylic acid (0.1 g, 0.529 mmol), acetonitrile (Volume: 10 ml) and N-ethyl-N-isopropylpropan-2-amine (0.157 g, 1.216 mmol) at room temperature with stirring until a solution was observed. Then, di(1H-imidazol-1-yl)methanone (0.094 g, 0.581 mmol) was added in one portion and the mixture was held for 4 h. Then the amine(S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile 2,2,2-trifluoroacetate (0.198 g, 0.740 mmol) was added in one portion. The mixture was heated to 75° C., held at 75° C. for 5 h, cooled to room temperature, and stirred at room temperature overnight. The volatiles were evaporated and the residue was redissolved in EtOAc, washed with 0.3N citric acid, saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified using column chromatography with ethyl acetate-methanol (95-5) mixture to yield the product (0.076 g, 44%)

Provenance & Evidence