(4-{2-[(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl]ethoxy}phenyl)acetic acid (70 mg, 0.165 mmol), 1-hydroxybenzotriazole hydrate (37.8 mg, 0.247 mmol), 3-hydroxyazetidine hydrochloride (27 mg, 0.247 mmol) and (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride (44.3 mg, 0.247 mmol) were dissolved in CH2Cl2 (4 ml). The mixture was stirred at RT for 5 min. and triethylamine (0.078 ml, 0.556 mmol) added. The mixture was stirred at RT overnight and the mixture loaded directly onto a preparative TLC plate that was developed with 10% MeOH in EtOAc. The desired product (Rf=0.35 @ 10% MeOH in EtOAc) was collected to give the title compound. 1H NMR (500 MHz, CDCl3) δ 8.30 (s, 2H), 7.20 (d, 2H), 6.85 (d, 2H), 4.70 (m, 2H), 4.55 (broad, s, 1H), 4.22 (s, 2H), 4.10 (m, 1H), 4.05 (m, 2H), 3.85 (m, 2H), 3.40 (s, 2H), 3.35 (s, 3H), 2.85 (m, 2H), 2.05 (m, 1H), 1.95 (m, 2H), 1.55 (m, 1H), 1.38 (m, 2H), 1.10 (m, 1H), 0.95 (m, 1H), 0.68 (m, 2H), −0.40 (m, 1H). LC/MS (m/z): 481 (M+H)+, GPR119 Human EC50: 7.7 nM.
