Azetidine → 1-methylcyclopropyl 4-[(1R,2S)-2-(2-{4-[2-(azetidin-1-yl)-2-oxoethyl]-3-fluorophenoxy}ethyl)cyclopropyl]piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of (2-fluoro-4-{2-[(1S,2R)-2-(1-{[(1-methylcyclopropyl)oxy]carbonyl}piperidin-4-yl)cyclopropyl]ethoxy}phenyl)acetic acid (100 mg, 0.238 mmol) in 1 ml anhydrous DMF at RT was added azetidine (16.3 mg, 0.286 mmol) and N,N-diisopropylethylamine (0.125 ml, 0.715 mmol). o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (181 mg, 0.477 mmol) was added into the solution and stirred at RT for 4 hrs. The reaction mixture was filtered and purified by reverse-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 35-95% acetonitrile in 0.1% formic acid in water gradient) to give the title compound. LC/MS (m/z): 459.3 (M+H)+. GPR119 Human EC50: 3.3 nM

Provenance & Evidence