Реакция #560799

Уравнение реакции

N-(4-(3-chloropyrazin-2-yloxy)-phenyl)pyridin-2-amine

Piperidine-4-carbonitrile

→

1-(3-(4-(pyridin-2-ylamino)-phenoxy)pyrazin-2-yl)piperidine-4-carbonitrile

Растворители

water

DMSO

Условия реакции

Обработка

1. 1
   ДругоеIn a 50 mL round-bottomed flask was placed
2. 2
   Другоеwas brought to 80° C.
3. 3
   Экстракцияextracted with DCM (3×10 mL)
4. 4
   ЭкстракцияThe organic extract
5. 5
   Промывкаwas washed with water (3×10 mL), satd sodium chloride solution (3×10 mL)
6. 6
   Сушкаdried with magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated
9. 9
   Другоеchromatographed through a Biotage™ pre-packed silica gel column (25M)
10. 10
    Промывкаeluting with a gradient of 1% to 5% methanol in DCM

Методика

In a 50 mL round-bottomed flask was placed N-(4-(3-chloropyrazin-2-yloxy)-phenyl)pyridin-2-amine (0.2376 g, 0.7954 mmol) in DMSO. Piperidine-4-carbonitrile (0.4363 g, 3.977 mmol) was added and the temperature was brought to 80° C. to stir overnight. The reaction mixture was diluted with water (10 mL) and extracted with DCM (3×10 mL). The organic extract was washed with water (3×10 mL), satd sodium chloride solution (3×10 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (25M), eluting with a gradient of 1% to 5% methanol in DCM, to provide 1-(3-(4-(pyridin-2-ylamino)-phenoxy)pyrazin-2-yl)piperidine-4-carbonitrile. MS (ESI, pos. ion) m/z: 373.1 (M+1). IC50 (uM) 0.006048.

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