Dimethylformamide → 6-[1-(6-Bromo-1H-1,2,3-triazolo[4,5-b]pyrazin-1-yl)ethyl]quinoline

Temperature

0 °C

To a solution of the 5-bromo-N*3*-(1-quinolin-6-yl-ethyl)-pyrazine-2,3-diamine in anhydrous DMF (25 mL) was added isoamyl nitrile (0.98 mL, 1.2 mmol) at 0° C. The reaction was stirred at 0° C. for 5 min, then the ice bath was removed and allowed to stir at ambient temperature for 5 min. The reaction was then heated at 70° C. for 1 hour, cooled and quenched with sat. aqueous solution of Na2SO3 (10 mL). Water (50 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (4×100 mL). The combined organics were washed with NaHCO3 (50 mL) and water (3×50 mL), dried over Na2SO4, filtered and concentrated to give 6-[1-(6-bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)-ethyl]-quinoline (1.56 g, 72% yield).

1. customthe ice bath was removed
2. stirringto stir at ambient temperature for 5 min
3. temperatureThe reaction was then heated at 70° C. for 1 hour
4. temperaturecooled
5. customquenched with sat. aqueous solution of Na2SO3 (10 mL)
6. additionWater (50 mL) and EtOAc (50 mL) were added
7. customThe organic layer was separated
8. extractionthe aqueous layer was extracted with EtOAc (4×100 mL)
9. washThe combined organics were washed with NaHCO3 (50 mL) and water (3×50 mL)
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-a1afd8b563a74cd8bb74efd5050a6a97

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07732604B2