Diethyl Ether → HCID 57527238, compound

To a solution of 2,6-dichloropyridin-3-amine (3.71 g, 22.8 mmol, 1.0 eq.) and isopropyl isothiocyanate (2.5 mL, 23.5 mmol, 1.0 eq.) in DMF (57 mL) under nitrogen at 0° C. was added NaH (95% in mineral oil, 0.77 g, 30.5 mmol, 1.3 eq.). After 10 min., the cold bath was removed, and the reaction mixture was stirred to room temperature for 10 min. It was then heated at 68° C. overnight. After cooling to 0° C., isopropyl isothiocyanate (1.5 mL) and NaH (0.44 g) were added, and heating was resumed. After 7.25 h, the reaction was cooled to room temperature. At 0° C., aqueous HCl (1 N), water and EtOAc were added, and the reaction mixture was stirred. The layers were separated, and the organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. Trituration with Et2O afforded 5-chloro-N-isopropylthiazolo[5,4-b]pyridin-2-amine as a white solid (3.43 g, 66% yield).

1. customthe cold bath was removed
2. temperatureIt was then heated at 68° C. overnight
3. temperatureAfter cooling to 0° C.
4. additionisopropyl isothiocyanate (1.5 mL) and NaH (0.44 g) were added
5. temperatureheating
6. waitAfter 7.25 h
7. temperaturethe reaction was cooled to room temperature
8. additionAt 0° C., aqueous HCl (1 N), water and EtOAc were added
9. stirringthe reaction mixture was stirred
10. customThe layers were separated
11. washthe organic layer was washed with saturated aqueous NaHCO3 and brine
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated in vacuo

ORD record

ord-68b644554bf84ffdb3fcb91e0f54c833

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994337B2