Azetidine → 1-(azetidin-1-yl)-2-[4-(2-{(1S,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-fluorophenyl]ethanone

Participants

Reaction Steps

To a solution of [4-(2-{(1S,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethoxy)-2-fluorophenyl]acetic acid (20.0 mg, 0.047 mmol) in 1 ml anhydrous DMF at RT was added azetidine (4.01 mg, 0.070 mmol) and N,N-diisopropylethylamine (0.201 ml, 1.15 mmol). o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (30.2 mg, 0.234 mmol) was added and the mixture stirred at RT for 4 hrs. The mixture was filtered and purified by reversed-phase HPLC (SunFire Prep C18 OBD 5 um 19×100 mm column; 45-90% acetonitrile in 0.1% formic acid in water gradient) to afford the title compound. LC/MS (m/z): 467.2 (M+H)+. GPR119 Human EC50: 0.40 nM.

Provenance & Evidence