Potassium Carbonate → 1-[1-(4-Fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[4-(trifluoromethyl)imidazol-1-yl]pyrrolidin-2-one

온도

60 °C

A mixture of 3-bromo-1-[1-(4-fluorophenyl)-5-isopropyl-pyrazol-4-yl]pyrrolidin-2-one (0.020 g, 0.055 mmol), 4-(trifluoromethyl)-1H-imidazole (0.024 g, 0.17 mmol) and K2CO3 (0.030 g, 0.22 mmol) in DMF (0.6 mL) was stirred at 60° C. for 1 hr. The mixture was then cooled to room temperature, quenched with water (30 mL) and extracted with EtOAc (50 mL). The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to yield the title compound (0.022 g, TFA salt, 75%); 1H NMR (TFA salt) (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.59 (s, 1H), 7.51 (s, 1H), 7.39 (dd, J=8.4, 4.8 Hz, 2H), 7.20 (dd, J=8.6, 8.6 Hz, 2H), 5.06 (dd, J=10.8, 8.8 Hz, 1H), 3.90 (m, 1H), 3.83 (m, 1H), 2.98 (m, 2H), 2.54 (m, 1H), 1.21 (d, J=7.2 Hz, 3H), 1.20 (d, J=7.2 Hz, 3H); MS: (ES) m/z calculated for C20H19F4N5O (free form) [M+H]+ 422.1. found 422.1.

1. temperatureThe mixture was then cooled to room temperature
2. customquenched with water (30 mL)
3. extractionextracted with EtOAc (50 mL)
4. customThe organic layer was separated
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo
7. custompurified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

ORD 기록

ord-0c46512a0bfe4baf9337ce0ce2e8ee95

출처 데이터셋

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09328116B2