1-Hydroxybenzotriazole → 3-[4-(2-chloro-phenylamino)-piperidin-1-yl]-3-oxo-N-(5-phenyl-thiazol-2-yl)-propionamide

Participants

Reaction Steps

To a stirred solution of N-(5-phenyl-thiazol-2-yl)-malonamic acid (0.075 g, 0.00028 mole) in DMF (2 mL) was added DIPEA (0.11 g, 0.00085 mole), HOBt (0.038 g, 0.00028 mole) and EDCI.HCl (0.065 g, 0.00034 mol). After 2 minutes (2-chloro-phenyl)-piperidin-4-yl-amine dihydrochloride (0.077 g, 0.00031 mol) 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. The residue was recrystallized from a mixture of ethyl acetate and hexane to afford 0.035 g (28%) of 3-[4-(2-chloro-phenylamino)-piperidin-1-yl]-3-oxo-N-(5-phenyl-thiazol-2-yl)-propionamide. LC-MS purity: 455.11 (M+1)+, 98.03%, 1H NMR (CDCl3): δ 11.6 (s, 1H), 7.9 (d, 2H), 7.4 (t, 3H), 7.3 (t, 2H), 7.2 (m, 2H), 7.1, 6.70 (m, 2H), 4.5 (d, 1H), 4.2 (d, 1H), 3.9 (d, 1H), 3.6 (s, 3H), 3.3 (t, 1H), 3.1 (t, 1H), 2.2 (s, 2H), 1.5 (m, 2H).

Provenance & Evidence