1-Hydroxybenzotriazole → HCID 178523486, compound

Participants

Reaction Steps

To a stirred solution of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid (0.1 g, 0.00049 mol) in DMF (5 mL) was added DIPEA (0.253 g, 0.00196 mol), HOBt (0.0827 g, 0.00061 mol) and EDCI.HCl (0.117 g, 0.00061 mol) at ambient temperature. After 5 minutes 2-amino-1-[4-(2-chloro-phenylamino)-piperidin-1-yl]-ethanone dihydrochloride (0.164 g, 0.00054 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 0.092 g (41%) of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 426.16 (M+1)+, 91.47%, 1H NMR (DMSO-d6): δ 13.5 (s, 1H), 9.7 (s, 1H), 8.0 (s, 1H), 7.58 (d, 2H), 7.1 (m, 2H), 6.8 (m, 4H), 6.56 (m, 1H), 4.9 (d, 1H), 4.3 (d, 1H), 4.1 (d, 2H), 3.8 (m, 11H), 3.6 (m, 11H), 3.1 (m, 1H), 2.7 (m, 1H), 1.9 (m, 2H), 1.3 (m, 2H)

Provenance & Evidence