Dichloromethane → HCID 46908239, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(2-(chloromethyl)pyridin-4-yl)-5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazole (0.097 g; 0.24 mmol), sarcosine t-butyl ester hydrochloride (0.037 g; 0.27 mmol) and K2CO3 (0.043 g; 0.27 mmol) in dioxan (3 mL) was heated at 70° C. for 7 days. DCM and water were added to the reaction mixture. The mixture was poured through a hydrophobic frit. The solvent was evaporated in vacuo. The material was purified by SCX chromatography and the material treated with HCl solution in dioxan (5 M; 3 mL) and the reaction mixture stirred at 70° C. for 18 hours. The solvent was evaporated in vacuo and the residue purified by preparative HPLC, affording the title product as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.78 (1 H, d, J=5.1 Hz), 8.42 (1 H, s), 8.16 (1 H, dd, J=8.2, 2.0 Hz), 8.08 (1 H, s), 8.04 (1 H, dd, J=5.2, 1.5 Hz), 7.38-7.21 (4 H, m), 7.12 (1 H, d, J=7.4 Hz), 5.39 (1 H, br s), 4.23 (2 H, dd, J=17.0, 12.7 Hz), 4.17 (2 H, s), 3.54 (2 H, s), 3.34 (3 H, s), 2.66 (3 H, s), 2.08 (3 H, s). LC/MS: 388 (M+H)+. HPLC (Method B) Rt 2.97 min (Purity: 99.2

Provenance & Evidence