Azetidine → 4-[(1R,2S)-2-{2-[4-(2-azetidin-1-yl-2-oxoethyl)phenoxy]ethyl}cyclopropyl]-1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]piperidine

Participants

Reaction Steps

2-(4-(2-((1S,2R)-2-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)cyclopropyl)ethoxy)phenyl)acetic acid (100 mg, 0.242 mmol), 1-hydroxybenzotriazole hydrate (55 mg, 0.363 mmol), and (E)-3-(ethyldiazenyl)-N,N-dimethylpropan-1-amine hydrochloride (70.0 mg, 0.363 mmol) were dissolved in CH2Cl2 (4 ml). The mixture was stirred at RT for 5 min. and azetidine (21 mg, 0.363 mmol) was added. The mixture was stirred at RT overnight and loaded directly on Preparative TLC that was developed with 5% MeOH in DCM. The desired product (Rf=0.35 @ 5% MeOH in DCM) was collected to give the title compound. 1H NMR (500 MHz, CDCl3) δ 7.20 (d, 2H), 6.90 (d, 2H), 4.05-4.15 (m, 8H), 3.41 (s, 2H), 3.05 (m, 2H), 2.96 (m, 1H), 2.26 (m, 2H), 2.18 (m, 1H), 1.95 (m, 2H), 1.50 (m, 3H), 1.35 (d, 6H), 0.95-1.05 (m, 2H), 0.68 (m, 2H), −0.40 (m, 1H). LC/MS (m/z): 453 (M+H)+, GPR119 Human EC50: 1.8 nM.

Provenance & Evidence