1,2-Dimethoxyethane → 5-[2-(Acetoxymethyl)-3-(4-methyl-5-oxo-6-{[4-(piperidin-4-yl)phenyl]-amino}-4,5-dihydropyrazin-2-yl)phenyl]-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-6-one

Temperatur

130 °C

A 10 mL microwave vial with a magnetic stirrer was charged with 111a (173 mg, 0.36 mmol), 121a (139 mg, 0.3 mmol), 1M sodium carbonate solution (1.2 mL, 1.2 mmol) and 1,2-dimethoxyethane (3 mL). After bubbling nitrogen through the resulting suspension for 10 min, tetrakis(triphenylphosphine)-palladium(0) (18 mg, 0.015 mmol) was added. The reaction mixture was heated at 130° C. for 15 minutes in the microwave reactor. After this time, ethyl acetate (15 mL) and water (10 mL) were added, and the layers were separated. The aqueous layer was extracted with Ethyl acetate (2×20 mL), and the combined organic layers were washed with brine and dried over sodium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by flash column chromatography (silica, ethyl acetate/hexanes) to afford compound 121b as yellow oil (240 mg).

1. customAfter bubbling nitrogen through the resulting suspension for 10 min
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with Ethyl acetate (2×20 mL)
4. washthe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. customThe drying agent was removed by filtration
7. concentrationThe filtrate was concentrated under reduced pressure
8. customthe resulting residue was purified by flash column chromatography (silica, ethyl acetate/hexanes)

ORD-Eintrag

ord-42d1c69d7e2343d6ae21a8d76f73b441

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08618107B2