1-Hydroxybenzotriazole → HCID 57874411, compound

Participants

Reaction Steps

To a stirred solution of N-(6-phenyl-pyridin-3-yl)-malonamic acid (0.07 g, 0.00024 mole) in DMF (1 mL) was added DIPEA (0.153 g, 0.00120 mole), HOBt (0.039 g, 0.00029 mole) and EDCI.HCl (0.055 g, 0.00029 mole). After 2 minutes (2-chloro-phenylsulfanyl)-piperidin-4-yl-amine hydrochloride (0.076 g, 0.00029 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 organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 0.07 g (63%) of 3-[4-(2-chloro-phenylsulfanyl)-piperidin-1-yl]-3-oxo-N-(6-phenyl-pyridin-3-yl)-propionamide. LC-MS purity: 466.13 (M+1)+, 93.65%, 1H NMR (DMSO-d6): δ 10.5 (s, 1H), 8.8 (d, 1H), 8.2 (d, 1H), 8.1 (d, 2H), 8.0 (d, 1H), 7.6-7.2 (m, 6H), 4.3 (d, 1H), 3.9 (d, 1H), 3.6-3.5 (m, 3H), 3.0 (t, 1H), 2.0 (m, 2H), 1.7-1.6 (m, 1H), 1.5-1.4 (m, 1H).

Provenance & Evidence