1,2-Dichloroethane → 1-(1-(2-((5S)-2-(2-(2-morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Participants

Reaction Steps

2-(2-(2-(2-Morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (420.8 mg, 0.9 mmol), 1-(piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (545 mg, 1.872 mmol), EDC (360 mg, 1.878 mmol), HOBt (282 mg, 1.841 mmol) and DIEA (730 μL, 4.191 mmol) were stirred in DMF (6 mL) at RT. The mixture was diluted with EtOAc and washed with water and saturated sodium bicarbonate solution. The aqueous layer was back-extracted, the organic layers were combined, then washed with brine, dried (MgSO4), and concentrated in vacuo. The crude product was purified by reverse phase column chromatography with ACN/water to give 1-(1-(2-((5S)-2-(2-(2-morpholinoethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Provenance & Evidence