Pyridine → N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-4-fluorophenyl}-2,6-difluorobenzenesulfonamide

온도

0 °C

To a solution of 3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-4-fluoroaniline (7.4 g, 20.4 mmol) in DCM (200 mL) was added pyridine (4.85 g, 61.3 mmol) and cooled to 0° C. 2,6-Difluorobenzene-1-sulfonyl chloride (4.76 g, 22.5 mmol) in DCM (10 mL) was added dropwise to the mixture. The reaction was stirred at rt overnight. Then the reaction was washed with water (200 mL), and extracted with DCM (2×100 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtrated and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (petroleum ether:EtOAc 5:1) to afford the title compound of Step E (2.3 g, 7.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.56 (d, J=5.3 Hz, 1H), 7.62-7.75 (m, 1H), 7.20-7.32 (m, 5H), 6.92 (d, J=5.3 Hz, 1H), 1.40 (s, 9H). m/z (ES+): 539 [M+H]+.

1. washThen the reaction was washed with water (200 mL)
2. extractionextracted with DCM (2×100 mL)
3. washThe organic layer was washed with brine
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltrated
6. concentrationconcentrated under reduced pressure
7. customto give the crude product, which
8. customwas purified by column chromatography on silica gel (petroleum ether:EtOAc 5:1)

ORD 기록

ord-e39eb3edc30f4da2afdf8efce419b078

출처 데이터셋

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08415345B2