1-Hydroxybenzotriazole → 5-(2-hydroxy-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

Participants

Reaction Steps

To a stirred solution of 5-(2-hydroxy-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid (0.13 g, 0.0006 mol) in DMF (2 mL) was added DIPEA (0.308 g, 0.00234 mol), HOBt (0.101 g, 0.00075 mol) and EDCI.HCl (0.143 g, 0.00075 mol) at ambient temperature. After 5 minutes 2-amino-1-[4-(2-chloro-phenylamino)-piperidin-1-yl]-ethanone hydrochloride (0.181 g, 0.00060 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and recrystallized from ethyl acetate to afford 0.113 g (41%) of 5-(2-hydroxy-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 468.18 (M+1)+, 96.98%. 1H NMR (DMSO-d6): δ 10.2 (s, 1H), 8.7 (t, 1H), 7.7 (d, 1H), 7.4 (s, 1H), 7.1 (m, 3H), 6.8 (m, 3H), 6.6 (m, 1H), 4.9 (m, 1H), 4.3 (d, 1H), 4.1 (m, 4H), 3.9 (m, 1H), 3.6 (m, 1H), 3.1 (m, 1H), 2.7 (m, 1H), 1.9 (m, 2H), 1.4 (m, 2H).

Provenance & Evidence