1-Hydroxybenzotriazole → HCID 57874431, compound

Participants

Reaction Steps

To a stirred solution of N-biphenyl-4-yl-malonamic acid (0.1 g, 0.00039 mole) in DMF (3 mL) was added DIPEA (0.176 g, 0.0014 mole), HOBt (0.078 g, 0.00058 mole) and EDCI.HCl (0.11 g, 0.00058 mole). After 2 minutes (2-nitro-phenoxy)-piperidine hydrochloride (0.12 g, 0.00046 mole) 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 organic layers were dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using neutral aluminium oxide (5% methanol in chloroform) to afford 0.130 g (72%) of N-biphenyl-4-yl-3-[4-(2-nitro-phenoxy)-piperidin-1-yl]-3-oxo-propionamide. LC-MS purity: 460.18 (M+1)+, 95%, 1H NMR (DMSO-d6): δ 7.9 (m, 1H), 7.7 (m, 7H), 7.5 (m, 3H), 7.3 (m, 1H), 7.1 (m, 1H), 5.0 (m, 1H), 3.6 (m, 6H), 2.0 (m, 2H), 1.8 (m, 2H).

Provenance & Evidence