2-(2,6-difluoro-4-(2-((1S,2R)-2-(1-(5-methoxypyrimidin-2-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetic acid (80 mg, 0.179 mmol), 1-hydroxybenzotriazole hydrate (41.1 mg, 0.268 mmol), 3-hydroxyazetidine hydrochloride (29.4 mg, 0.268 mmol) and (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride (48.2 mg, 0.268 mmol) were dissolved in CH2Cl2 (4 ml). The mixture was stirred at RT for 5 min and triethylamine (0.075 ml, 0.536 mmol) was added. The mixture was stirred at RT overnight and purified by loading directly onto a Preparative TLC plate that was developed with pure EtOAc. The desired product (Rf=0.40 @ pure EtOAc) was collected to give the title compound. 1H NMR (500 MHz, CDCl3) δ 8.15 (s, 2H), 6.50 (d, 2H), 4.60 (m, 3H), 4.40 (m, 1H), 4.30 (m, 1H), 4.05 (m, 2H), 3.90 (m, 11-1), 3.80 (s, 3H), 3.41 (s, 2H), 3.05 (broad, s, 1H), 2.85 (m, 2H), 2.15 (m, 1H), 1.92 (m, 2H), 1.55 (m, 1H), 1.40 (m, 2H), 0.95 (m, 2H), 0.68 (m, 2H), −0.40 (m, 1H). LC/MS (m/z): 503 (M+H)+, GPR119 Human EC50: 0.59 nM.
