1-Chloroethyl chloroformate → 4-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-1,2,3,6-tetrahydropyridine hydrochloride

To a solution of 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine (i.e. the product of Example 13, Step B) (0.400 g, 0.99 mmol) in dichloroethane (10 mL) was added 1-chloroethyl chloroformate (0.286 g, 1.99 mmol), and the reaction mixture was heated to 80° C. for 5 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Methanol (10 mL) was added to the residue, and the resulting mixture was heated to 60° C. for 1 h, cooled to room temperature, and concentrated under reduced pressure. The residue was triturated with 50% of petroleum ether in ethyl acetate, and the solid formed was filtered and dried to give 0.25 g of the title compound as a white solid.

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationconcentrated under reduced pressure
3. additionMethanol (10 mL) was added to the residue
4. temperaturethe resulting mixture was heated to 60° C. for 1 h
5. temperaturecooled to room temperature
6. concentrationconcentrated under reduced pressure
7. customThe residue was triturated with 50% of petroleum ether in ethyl acetate
8. customthe solid formed
9. filtrationwas filtered
10. customdried

ORD record

ord-b2b7085ea8394723b338a7aa8248e666

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642634B2