Potassium Carbonate → (S)-N-[6-(3-Amino-pyrrolidin-1-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide

온도

130 °C

A mixture of 975 mg (1.83 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide, 1.26 g (9.15 mmol) potassium carbonate and 800 mg (3.66 mmol) (S)-3-(trifluoro-acetamido)pyrrolidine hydrochloride in 10 ml dimethyl sulfoxide was stirred at 130° C. for 52 h. After cooling to room temperature the reaction mixture was diluted with 30 ml tert-butyl methyl ether and washed with 20 ml of water and 10 ml of a saturated aqueous solution of sodium carbonate. The combined organic layers were dried over sodium sulfate and concentrated. The residue was dissolved in 25 ml of a 2 N solution of ammonia in ethanol. The solution was stirred at room temperature for 18 h. The reaction mixture was concentrated and purified by flash chromatography to give 640 mg (60%) of the title compound as a light brown foam.

1. temperatureAfter cooling to room temperature the reaction mixture
2. washwashed with 20 ml of water and 10 ml of a saturated aqueous solution of sodium carbonate
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in 25 ml of a 2 N solution of ammonia in ethanol
6. stirringThe solution was stirred at room temperature for 18 h
7. concentrationThe reaction mixture was concentrated
8. custompurified by flash chromatography

ORD 기록

ord-5495d80fbeee47ff8b01bac324d05dfb

출처 데이터셋

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07939533B2