Trifluoroacetic acid → HCID 86696617, compound

Temperature

90 °C

A mixture of ethyl 2-(5-bromo-3-(isopropylamino)pyrazin-2-ylamino)acetate (780 mg, 2.26 mmol), methanol (5 mL) and TFA (10 mL) in a sealable vessel was purged with nitrogen, sealed, stirred vigorously and heated at 90° C. with an oil bath for 16 h. The resulting mixture was diluted with methanol and the solvent was removed under reduced pressure. Methanol (10 mL) was added and the solvent was removed under reduced pressure again. Methanol (10 mL) and sodium bicarbonate were added. The resulting mixture was stirred at room temperature until pH=6 (in water), the solvent was removed under reduced pressure. Water (20 mL) was added. The mixture was extracted with methylene chloride (20 mL×3). The organic layer was dried over anhydrous sodium sulfate, concentrated to give the crude product and purified on silica column chromatography (10-20% ethyl acetate in petroleum ether) to give the title compound (360 mg, 39.4% yield).

1. customwas purged with nitrogen
2. customsealed
3. additionThe resulting mixture was diluted with methanol
4. customthe solvent was removed under reduced pressure
5. additionMethanol (10 mL) was added
6. customthe solvent was removed under reduced pressure again
7. additionMethanol (10 mL) and sodium bicarbonate were added
8. stirringThe resulting mixture was stirred at room temperature until pH=6 (in water)
9. customthe solvent was removed under reduced pressure
10. additionWater (20 mL) was added
11. extractionThe mixture was extracted with methylene chloride (20 mL×3)
12. dry with materialThe organic layer was dried over anhydrous sodium sulfate
13. concentrationconcentrated
14. customto give the crude product
15. custompurified on silica column chromatography (10-20% ethyl acetate in petroleum ether)

ORD record

ord-ba5c8de6c48e4146a581396125af23ab

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507492B2