3-Acetylpyridine → HCID 178523557, Verbindung

Beteiligte Stoffe

Reaktionsschritte

DIPEA (158.2 mg, 1.22 mmol) was added to a stirred solution of [(5-pyridin-3-yl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (prepared by the method used for the synthesis of Intermediate 30, starting from 3-acetylpyridine) (76 mg, 0.30 mmol) in DMF (2 mL) followed by HOBt (43.4 mg, 0.32 mmol) and EDCI (61.6 mg, 0.32 mmol). After 2 minutes of stirring, 3-(3-trifluoromethyl-phenoxy)-azetidine hydrochloride (77.5 mg, 0.3 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure The residue obtained purified by column chromatography (using silica gel 60- and 100% ethyl acetate as eluent) to afford 43 mg (32% Yield) of 5-pyridin-3-yl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-azetidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 446.14, 93.76%. 1H NMR (300 MHz, DMSO-d6): δ 9.44 (s, 1H), 9.2 (d, 1H), 8.72 (m, 2H), 8.38 (m, 1H), 7.64 (m, 1H), 7.52 (t, 1H), 7.35 (d, 1H), 7.16 (m, 2H), 5.2 (m, 1H), 4.7 (m, 1H), 4.3 (m, 1H), 4.2 (m, 1H), 3.95 (d, 2H), 3.8 (m, 1H).

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