Thiourea → HCID 58075094, compound

Ethyl 3-(5-chloropyrazin-2-yl)-3-oxopropanoate (Intermediate 45, 2.0 g, 8.77 mM) was dissolved in ethyl acetate (30 mL), to this amberlyst resin (2.0 g) and N-iodosuccinamide (2.1 g, 9.64 mM) were added and stirred for 1 h at room temperature. The resin was filtered and the filtrate was concentrated under reduced pressure to afford crude compound, which was dissolved in methanol (25 mL). Thiourea (0.99 g, 13.15 mM) was added to the reaction mixture and the reaction mixture was heated to reflux for 2 h. The methanol was concentrated under reduced pressure and the resulting residue was partitioned between sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (50 mL). The organic layers were combined and dried over anhydrous sodium sulphate, filtered, concentrated under reduced pressure to obtain crude compound which was purified by flash column chromatography (gradient up to 50% of ethyl acetate/pet ether) to afford 500 mg (20.06%) of ethyl 2-amino-4-(5-chloropyrazin-2-yl)-1,3-thiazole-5-carboxylate off-white solid.

1. additionwere added
2. filtrationThe resin was filtered
3. concentrationthe filtrate was concentrated under reduced pressure
4. customto afford crude compound, which
5. temperaturethe reaction mixture was heated
6. temperatureto reflux for 2 h
7. concentrationThe methanol was concentrated under reduced pressure
8. customthe resulting residue was partitioned between sodium bicarbonate solution (50 mL)
9. extractionextracted with ethyl acetate (50 mL)
10. dry with materialdried over anhydrous sodium sulphate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customto obtain crude compound which
14. customwas purified by flash column chromatography (gradient up to 50% of ethyl acetate/pet ether)

ORD record

ord-410ce3b48c3f492896274742737cdc87

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071605B2