Boron trifluoride etherate → 5-[1,2,4]Oxadiazol-3-yl-4-phenyl-thiazol-2-ylamine

2-Amino-N-hydroxy-4-phenyl-thiazole-5-carboxamidine (1.0 g, 4.3 mmol) was dissolved in methanol (20 mL), and trimethyl orthoformate (1.2 mL, 11 mmol) containing boron trifluoride etherate (0.2 mL, 1.6 mmol) was added End the mixture was heated at reflux for 3 h. The reaction mixture was cooled, and the solvent was removed under reduced pressure at 20° C. The residue was extracted with ethyl acetate, and the solution was washed with saturated aqueous NaHCO3 dried over sodium sulfate and evaporated. The crude product was purified by flash column chromatography, eluted with the gradient of 10-18% ethyl acetate in hexanes to get the product (the product was eluted by 18% ethyl acetate in hexanes). Yield: 0.1 g, 10%

1. additionwas added End the mixture
2. temperaturewas heated
3. temperatureat reflux for 3 h
4. temperatureThe reaction mixture was cooled
5. customthe solvent was removed under reduced pressure at 20° C
6. extractionThe residue was extracted with ethyl acetate
7. washthe solution was washed with saturated aqueous NaHCO3
8. dry with materialdried over sodium sulfate
9. customevaporated
10. customThe crude product was purified by flash column chromatography
11. washeluted with the gradient of 10-18% ethyl acetate in hexanes
12. customto get the product (the product
13. washwas eluted by 18% ethyl acetate in hexanes)

ORD record

ord-8612bbdd79c941c89633a3cc64e1ce84

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910613B2