1-Hydroxybenzotriazole → HCID 57874366, compound

Participants

Reaction Steps

DIPEA (133 mg, 1.03 mmol) was added to a stirred solution of 5-(3-hydroxy-phenyl)-isoxazole-3-carboxylic acid (61 mg, 0.294 mmol)) (prepared by the method used for the synthesis of Intermediate 25, starting from 2′-benzyloxyacetophenone) in DMF (2 mL) followed by HOBt (41.7 mg, 0.308 mmol) and EDCI.HCl (59 mg, 0.308 mmol). After 2 minutes 2-amino-1-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (99 mg, 0.294 mmol) (prepared according to Step 1 and 5 of the General Scheme) 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, dried over sodium sulfate and concentrated under reduced pressure The residue was purified by washing with ethylacetate to afford 54 mg (37.7% Yield) of 5-(3-hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-oxo-2-[4-(3-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 490, 94.4%. 1H NMR (300 MHz, DMSO-d6): δ9.9 (s, 1H), 8.65 (t, 1H), 7.5 (t, 1H), 7.3 (m, 7H), 6.95 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.9 (s, 1H), 3.7 (m, 1H), 3.4 (m, 2H), 2.0 (m, 2H), 1.6 (m, 2H).

Provenance & Evidence