反应详情

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).

1. customprepared by the method
2. stirringthe resulting mixture was stirred at room temperature overnight
3. extractionextracted with ethyl acetate
4. dry with materialThe organic layer was dried over sodium sulfate
5. concentrationconcentrated under reduced pressure The residue
6. customobtained
7. custompurified by column chromatography (using silica gel 60- and 100% ethyl acetate as eluent)