1-Hydroxybenzotriazole → HCID 178523518, compound

Participants

Reaction Steps

DIPEA (226 mg, 1.75 mmol) was added to a stirred solution of {[5-(4-fluoro-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (130 mg, 0.5 mmol) (prepared by the method used for the synthesis of Intermediate 30, starting from (4-fluorophenyl)acetophenone) in DMF (2 mL) followed by HOBt (71 mg, 0.52 mmol) and EDCI.HCl (100 mg, 0.52 mmol). After 2 minutes 3-chloro-5-(piperidin-4-yloxy)-pyridine hydrochloride (125 mg, 0.5 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 The residue was purified by column chromatography (using 60-120 silica gel and 40% ethyl acetate in hexane as eluent) to afford 134 mg (58.5% Yield) of 5-(4-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 458, 93.27%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (s, 1H), 8.0 (m, 2H), 7.8 (m, 2H), 7.7 (d, 1H), 7.4 (m, 1H), 7.25 (m, 2H), 7.1 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 1.9 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence