反应详情

DIPEA (158.2 mg, 1.22 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (75 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 followed by extraction with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated under reduced pressure to afford the residue. The residue was purified by column chromatography (using silica gel 60- and 100% ethyl acetate as eluent) to afford 69 mg (51.1% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[3-(3-trifluoromethyl-phenoxy)-azetidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 445.14, 90.72%. 1H NMR (300 MHz, DMSO-d6): δ 14.8 (s, 1H), 8.2 (t, 1H), 7.78 (t, 2H), 7.5 (t, 1H), 7.3 (m, 5H), 7.16 (d, 2H), 7.1 (d, 1H), 5.18 (m, 1H), 4.64 (q, 1H), 4.36 (m, 1H), 4.18 (m, 1H), 3.84 (m, 3H).

1. stirringthe resulting mixture was stirred at room temperature overnight
2. extractionfollowed by extraction with ethyl acetate
3. dry with materialThe organic phase was dried over sodium sulfate
4. concentrationconcentrated under reduced pressure
5. customto afford the residue
6. customThe residue was purified by column chromatography (using silica gel 60- and 100% ethyl acetate as eluent)