1-Hydroxybenzotriazole → HCID 178523514, compound

Participants

Reaction Steps

DIPEA (150 mg, 1.2 mmol) was added to a stirred solution of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid (70 mg, 0.34 mmol) in DMF (2 mL) followed by HOBt (48 mg, 0.36 mmol) and EDCI.HCl (69 mg, 0.36 mmol). After 2 minutes 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (116 mg, 0.34 mmol) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, extracted with ethyl acetate and dried over sodium sulfate. The organic layer was concentrated under reduced pressure to afford the residue. The residue was purified by washing with 1% MeOH in EtOAc to afford 92 mg (55% Yield) of 5-(4-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 489, 96%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 9.8 (s, 1H), 8.02 (t, 1H), 7.5 (m, 3H), 7.28 (t, 3H), 6.8 (m, 3H), 4.8 (m, 1H), 4.2 (d, 2H), 3.9 (m, 1H), 3.6 (m, 1H), 3.4 (m, 1H), 3.2 (m, 1H), 2.0 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence