1-Hydroxybenzotriazole → HCID 57874499, compound

Participants

Reaction Steps

To a stirred solution of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-3-oxo-propionic acid (0.1 g, 0.00034 mole) in DMF (2 mL) was added DMAP (0.063 g, 0.00051 mole), HOBt (0.055 g, 0.00041 mole) and EDCI.HCl (0.079 g, 0.00041 mole). After 2 minutes 4-[1, 2, 4]-oxadiazol-3-yl-phenylamine (0.06 g, 0.00037 mole) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the product was extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to afford 0.09 g (61%) of 3-[4-(2-chloro-phenoxy)-piperidin-1-yl]-N-(4-[1,2,4]oxadiazol-3-yl-phenyl)-3-oxo-propionamide. LC-MS purity: 441 (M+1)+, 94.4%, 1H NMR (CDCl3): δ 10.5 (s, 1H), 8.8 (s, 1H), 8.1 (d, 2H), 7.74 (d, 2H), 7.4 (d, 1H), 7.2 (d, 1H), 6.96 (t, 2H), 4.7 (q, 1H), 4.1 (m, 1H), 3.8 (m, 1H), 3.6 (m, 2H), 3.55 (s, 2H), 2.0 (m, 5H).

Provenance & Evidence