Thiazolidine → HCID 57657253, compound

Participants

Reaction Steps

A round bottom flask, equipped with a stir bar, was charged with 3-[4-amino-2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoic acid (500 mg, 1.40 mmol), anhydrous pyridine (50 mL) and 1-hydroxybenzotriazole (379 mg, 2.80 mmol). After 30 minutes of stirring 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (537 mg, 2.80 mmol) was added to the reaction mixture in two portions. After 15 minutes, thiazolidine (250 mg, 2.80 mmol) was added in one portion. The pale yellow solution was stirred for 18 hours and then concentrated under reduced pressure. The resulting foam was dissolved in dichloromethane and washed with 1% aqueous sodium carbonate (2×15 mL). The combined aqueous fractions were extracted with chloroform (3×30 mL). The combined organic fractions were purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-25% gradient of CMA in chloroform) followed by recrystallization from acetonitrile to provide 516 mg of 1-{4-amino-2-ethyl-7-[3-oxo-3-(1,3-thiazolidin-3-yl)propyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as a white solid, mp 210-212° C.

Provenance & Evidence