4'-Fluoroacetophenone → HCID 57874463, compound

Participants

Reaction Steps

DIPEA (186 mg, 1.43 mmol) was added to a stirred solution of {[5-(4-fluoro-phenyl)-isoxazole-3-carbonyl]-amino}-acetic acid (76 mg, 0.29 mmol) (prepared by the method used for the synthesis of Intermediate 26, starting from 4′-fluoroacetophenone) in DMF (2 mL) followed by HOBt (41 mg, 0.3 mmol) and EDCI.HCl (58 mg, 0.3 mmol). After 2 minutes 2-chloro-3-(piperidin-4-yloxy)-pyridine hydrochloride (72 mg, 0.29 mmol) (prepared by method used for the synthesis of Intermediate 15) 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. Purification by recrystallisation from 10% ethyl acetate in hexane to afford 66 mg (50% Yield) of 5-(4-fluoro-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 459, 94.53%. 1H NMR (300 MHz, DMSO-d6): δ 8.65 (s, 1H), 7.98 (m, 3H), 7.72 (m, 1H), 7.38 (m, 4H), 4.8 (m, 1H), 4.2 (d, 2H), 3.7 (m, 2H), 3.4 (m, 2H), 1.9 (m, 2H), 1.6 (m, 2H).

Provenance & Evidence