1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86651053, compound

To a mixture of 0.58 g of WSC and 5 ml of pyridine 5 ml, 0.48 g of 3-chloroisonicotinic acid was added. The reaction mixture was stirred at room temperature for 25 minutes. To the reaction mixture, 0.75 g of 2-amino-4-(heptafluoroisopropyl)phenol was added and was stirred while heating at 60° C. for three hours. The reaction mixture was cooled to room temperature, the 0.24 g of 3-chloroisonicotinic acid and 0.29 g of WSC was added and stirred while heating at 60° C. for 1.5 hours and then at 80° C. for 1.3 hours. The mixture reaction was cooled to room temperature, and then concentrated under reduced pressure. Then, water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.90 g of 3-chloro-N-[2-hydroxy-5-(heptafluoroisopropyl)phenyl]isonicotinamide.

1. additionwas added
2. stirringwas stirred
3. temperaturewhile heating at 60° C. for three hours
4. temperatureThe reaction mixture was cooled to room temperature
5. stirringstirred
6. temperaturewhile heating at 60° C. for 1.5 hours
7. waitat 80° C. for 1.3 hours
8. customThe mixture reaction
9. temperaturewas cooled to room temperature
10. concentrationconcentrated under reduced pressure
11. additionThen, water was added to the residue
12. extractionfollowed by extraction with ethyl acetate twice
13. washThe combined organic layers were washed with a saturated sodium chloride solution
14. dry with materialwas dried over anhydrous sodium sulfate
15. concentrationconcentrated under reduced pressure

ORD record

ord-1a5f2f93bb264402a534229dc3c69053

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609705B2