Ethyl 5-phenylthiazole-2-carboxylate → (S)-Methyl 3-methyl-2-(1-oxo-6-(4-(5-phenylthiazole-2-carboxamido)phenyl)isoindolin-2-yl)butanoate

Temperatur

80 °C

To a solution of the compound of example 6 (405 mg, 1.2 mmol) and ethyl 5-phenylthiazole-2-carboxylate (233 mg, 1 mmol) in toluene (15 mL) in a sealed tube, was added 2M solution of AlMe3 (135 mg, 1.875 mmol) and the reaction mixture was heated at 80° C. for 2 h. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with saturated ammonium chloride. The resulting solution was extracted with ethyl acetate. The ethyl acetate extract was washed with water, brine, dried over anhydrous sodium sulphate and concentrated to obtain a crude material, which was purified using column chromatography (30% ethyl acetate in petroleum ether) to afford the title compound.

1. customAfter completion of the reaction
2. temperaturethe reaction mixture was cooled to room temperature
3. customquenched with saturated ammonium chloride
4. extractionThe resulting solution was extracted with ethyl acetate
5. extractionThe ethyl acetate extract
6. washwas washed with water, brine
7. dry with materialdried over anhydrous sodium sulphate
8. concentrationconcentrated
9. customto obtain a crude material, which
10. customwas purified

ORD-Eintrag

ord-47294878b9a44157bda3f11ae5d882a4

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08748426B2