Water → HCID 67135827, compound

Participants

Reaction Steps

To a solution of (4-(5-(4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methanol (0.125 g; 0.30 mmol) and DIEA (0.10 mL; 0.60 mmol) in DCM (2.5 mL) was added methanesulfonyl chloride (0.026 mL; 0.33 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Water was added to the reaction mixture and the mixture poured through a hydrophobic frit. The solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc) to afford the title product (0.129 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 8.77 (1 H, dd, J=5.1, 0.9 Hz), 8.51 (1 H, d, J=2.1 Hz), 8.34 (1H, dd, J=8.4, 2.1 Hz), 8.23 (1 H, s), 7.99 (1 H, dd, J=5.1, 1.6 Hz), 7.56 (1 H, d, J=8.4 Hz), 4.78 (2 H, s), 3.12-3.03 (2 H, m), 2.59 (1 H, td, J=11.0, 3.1 Hz), 1.86-1.62 (4 H, m), 1.53-1.38 (2 H, m), 0.86 (3 H, d, J=6.2 Hz).

Provenance & Evidence