Dimethylformamide → HCID 22252428, compound

A solution of 4-chloro-1,3-dimethylpyrazolo[5,4-b]pyridine-5-carboxylic acid (450 mg) and morpholine (870 mg) in DMF (15 mL) was stirred at room temperature for 5 h, and then concentrated under reduced pressure. The residue was treated with water (10 mL), and the resulting solid was filtered, washed with water, and dried under high vacuum. The solid was suspended in anhydrous dichloromethane (20 mL) and treated with oxalyl chloride (1.0 mL) and anhydrous DMF (0.1 mL). The mixture was stirred at room temperature for 1 h, filtered, and the filtrate was concentrated under reduced pressure. The residue was cooled in an ice-bath and slowly treated with a saturated solution of ammonia in THF (20 mL). The suspension was removed from the ice-bath, stirred at room temperature for 1 h, and filtered. The solid was washed with water and dried under high vacuum to give 1,3-dimethyl-4-morpholin-4-ylpyrazolo[5,4-b]pyridine-5-carboxamide as a white powder. A portion of this material (0.33 g) was dissolved in hot toluene (30 mL) and azeotropic for 1 h. The solution was cooled to room temperature and treated with 4-fluoro-3-(trifluoromethyl)phenylisocyanate (0.27 g). The mixture was refluxed for 16 h and then cooled to room temperature. The precipitated solid was filtered, washed with toluene, and dried under high vacuum to give the title compound as a white powder.

1. concentrationconcentrated under reduced pressure
2. additionThe residue was treated with water (10 mL)
3. filtrationthe resulting solid was filtered
4. washwashed with water
5. customdried under high vacuum
6. additiontreated with oxalyl chloride (1.0 mL) and anhydrous DMF (0.1 mL)
7. filtrationfiltered
8. concentrationthe filtrate was concentrated under reduced pressure
9. temperatureThe residue was cooled in an ice-bath
10. additionslowly treated with a saturated solution of ammonia in THF (20 mL)
11. customThe suspension was removed from the ice-bath
12. stirringstirred at room temperature for 1 h
13. filtrationfiltered
14. washThe solid was washed with water
15. customdried under high vacuum

ORD record

ord-f88f4764f3644ec7bb4f88531fad711e

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06992086B2