Triethylamine → HCID 67048783, compound

Participants

Reaction Steps

200 mg (1.48 mmol) of 1-hydroxybenzotriazole and 284 mg (1.48 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride were added to a solution of 907 mg (1.48 mmol) of [5-cyano-3-(2-ethoxypyridin-3-yl)-2-oxo-2,3-dihydro-1H-indol-3-yl]acetic acid from example 1.6 in 10 ml of dimethylformamide. The mixture was stirred for 15 minutes and then 285 mg (1.56 mmol) of 1-methyl-4-piperidin-4-ylpiperazine and 1.03 ml (7.41 mmol) of triethylamine were added. The reaction mixture was stirred at room temperature overnight. The reaction was checked by TLC (silica gel, dichloromethane/methanol 15:5). The reaction mixture was mixed with water and diluted with ethyl acetate. The phases were separated and the aqueous phase was extracted with ethyl acetate (1×). The combined organic phase was washed with water (1×) and saturated sodium chloride solution (1×), dried over magnesium sulfate and filtered, and the solvent was evaporated in vacuo. The resulting residue was purified by preparative MPLC (ISCO Companion, 12 g NP cartridge) with dichloromethane/methanol (10-70%) as eluent. 497 mg (0.99 mmol, 66%) of the title compound were obtained as a colorless solid.

Provenance & Evidence