Dimethylformamide → HCID 178522061, compound

To a mixture of 0.80 g of 3-amino-2-hydroxy-6-trifluoromethylpyridine, 1.14 g of triethylamine and 10 ml of DMF, 0.88 g of isonicotinic acid chloride hydrochloride was added while ice-cooling. The reaction mixture was stirred at room temperature for one hour and further stirred while heating at 50° C. for one hour. To the reaction mixture, 0.88 g of isonicotinic acid chloride hydrochloride and 1.1 g of triethylamine were added, and the reaction mixture was stirred while heating at 50° C. for further 1.5 hours. The reaction mixture was cooled to room temperature, and water was added to the reaction mixture. Precipitated crystals were collected by filtration. The resultant solid was dissolved in ethyl acetate, then washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.91 g of N-[2-hydroxy-6-(trifluoromethyl)pyridin-3-yl]-isonicotinamide.

1. additionwas added while ice-
2. temperaturecooling
3. stirringfurther stirred
4. temperaturewhile heating at 50° C. for one hour
5. stirringthe reaction mixture was stirred
6. temperaturewhile heating at 50° C. for further 1.5 hours
7. temperatureThe reaction mixture was cooled to room temperature
8. customPrecipitated crystals
9. filtrationwere collected by filtration
10. dissolutionThe resultant solid was dissolved in ethyl acetate
11. washwashed with a saturated sodium chloride solution
12. dry with materialdried over anhydrous magnesium sulfate
13. concentrationconcentrated under reduced pressure

ORD record

ord-dd708bc4ac5d4633a37e70ac0bec942f

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445522B2