Triethylamine → HCID 178522346, compound

Temperature

0 °C

To a stirred solution of 3-aminopyrazole (60 g, 0.722 mol, ABCR) in acetonitrile (500 ml) at 0° C. (ice/brine bath) was added, dropwise, triethylamine (201 ml, 1.44 mol) at such a rate to keep the temperature below 5° C. The reaction mixture was stirred at 0° C. for 0.5 h then a solution of 2,6-difluorobenzoyl chloride (127.5 g, 0.722 mol, Aldrich) in acetonitrile (200 ml) was added over approximately 1 h, keeping the temperature between 0-7° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure and the residue partitioned between water (250 ml) and EtOAc (500 ml). Some solid formed at the interface, this was filtered off and turned out to be product—combined with isolated product at the end for drying. The aqueous layer was separated and extracted with EtOAc (2×500 ml). The combined organics were washed with water (500 ml), dried (MgSO4), charcoaled, filtered and concentrated under reduced pressure to give a yellow solid. The combined residues were triturated with DCM (500 ml) then water (100 ml) and the solid collected by filtration and dried on the sinter, then under high vacuum overnight to give the title compound as a white solid (108.5 g);

1. customthe temperature below 5° C
2. custombetween 0-7° C
3. temperatureto warm to room temperature
4. stirringstirred overnight
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. customthe residue partitioned between water (250 ml) and EtOAc (500 ml)
7. customSome solid formed at the interface
8. filtrationthis was filtered off
9. customfor drying
10. customThe aqueous layer was separated
11. extractionextracted with EtOAc (2×500 ml)
12. washThe combined organics were washed with water (500 ml)
13. dry with materialdried (MgSO4)
14. filtrationfiltered
15. concentrationconcentrated under reduced pressure
16. customto give a yellow solid
17. customThe combined residues were triturated with DCM (500 ml)
18. filtrationwater (100 ml) and the solid collected by filtration
19. customdried on the sinter

ORD record

ord-a7b381f9343d469cab921a539fa23527

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399436B2