Triethylamine → HCID 21963694, compound

Participants

Reaction Steps

To a dry roundbottom flask add [3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-acetic acid (50 mg, 0.11 mmol), 3-amino-pyridine (16 mg, 0.17 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (33 mg, 0.17 mmol), 1-hydroxy-7-azabenzotriazole (23 mg, 0.17 mmol), 4-dimethylamino-pyridine (2 mg, 0.01 mmol), and dimethylformamide (3 mL). Stir the reaction under nitrogen, and add triethylamine (30 μL, 0.22 mmol) dropwise. Stir the solution under nitrogen at room temperature overnight. Concentrate the mixture, partition between 20% isopropanol/chloroform and water, and separate. Wash the organic layer with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform) to give 19.8 mg of the title compound as an orange solid, 33% yield. 1H NMR: consistent with structure. MS (ion spray) 452 (M+).

Provenance & Evidence