1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide

To a mixture of 0.44 g of WSC and 4 ml of pyridine, 0.36 g of 3-chloroisonicotinic acid was added. The reaction mixture was stirred at room temperature for 15 minutes. To the reaction mixture, 0.45 g of 2-amino-4-(pentafluoroethyl)phenol was added and stirred while heating at 60° C. for two hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.25 g of 3-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide.

1. additionwas added
2. stirringstirred
3. temperaturewhile heating at 60° C. for two hours
4. temperatureThe reaction mixture was cooled to room temperature
5. concentrationconcentrated under reduced pressure
6. additionWater was added to the residue
7. extractionfollowed by extraction with ethyl acetate twice
8. washThe combined organic layers were washed with water
9. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-85288721b9e9472d910ddf0ddf6f4fba

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609705B2