2-Aminothiazole → HCID 178522553, compound

A solution of 5.37 g of 2-amino-thiazole, 16.27 g of triethylamine and 214 ml of ethyl acetate were added with stirring over 25 minutes at 7° C. to a solution of 18.62 g of the product of Step F in 320 ml of ethyl acetate, and after the temperature returned to room temperature, the mixture was refluxed for one hour and cooled. The mixture was vacuum filtered and the filtrate was washed with water, dried and evaporated to dryness under reduced pressure at 40° C. The 19.22 gm of residue which was the triethylamine salt of the acid was taken up in 180 ml of 2 N sodium hydroxide solution and the mixture was refluxed for 3-4 minutes and was cooled. The mixture was vacuum filtered and the pH of the filtrate was adjusted to 1 by addition of 20% hydrochloric acid. The mixture was vacuum filtered and the recovered product was crystallized from acetic acid to obtain 8.22 g of 2,7-bis-(trifluoromethyl)-4-hydroxy-N-(2-thiazolyl)-3-quinolinecarboxamide melting at 270° C.

1. customreturned to room temperature
2. temperaturethe mixture was refluxed for one hour
3. temperaturecooled
4. filtrationfiltered
5. washthe filtrate was washed with water
6. customdried
7. customevaporated to dryness under reduced pressure at 40° C
8. temperaturethe mixture was refluxed for 3-4 minutes
9. temperaturewas cooled
10. filtrationfiltered
11. additionthe pH of the filtrate was adjusted to 1 by addition of 20% hydrochloric acid
12. filtrationfiltered
13. customthe recovered product was crystallized from acetic acid

ORD record

ord-99b39267754f437ea44df7a48207362f

Source dataset

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04299831