Diisopropylethylamine → 2-(4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)-1-(3-hydroxyazetidin-1-yl)ethanone

Participants

Reaction Steps

(4-{2-[(1S,2R)-2-{1-[5-(ethoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}-2-fluorophenyl)acetic acid (50, 0.109 mmol) and 3-hydroxy azetidine hydrochloride (11.97 mg, 0.109 mmol) were dissolved in DMF (1 ml) and HATU (83 mg, 0.219 mmol) and DIEA (0.057 ml, 0.328 mmol) added. The mixture was stirred at RT for 2 hr. The mixture was diluted with ethyl acetate (20 mL), washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, Biotage 25M, using a gradient eluant of MeOH/DCM (0-10%) to to provide the title compound. LC/MS (m/z): 513 (M+H)+. GPR119 Human EC50: 1.9 nM

Provenance & Evidence