Triethylamine → HCID 178522343, compound

To a solution of 1H-pyrazol-3-amine (249 mg, 3 mmol, Aldrich) in acetonitrile (10 ml) was added triethylamine (0.836 ml, 6.0 mmol, Aldrich) and the stirred solution cooled in an ice-water bath. A solution of 2-fluorobenzoyl chloride (0.358 ml, 3.0 mmol, Alfa Aesar) in acetonitrile (10 ml) was added dropwise. The mixture was stirred under nitrogen and allowed to warm slowly to ambient temperature overnight. The solvent was concentrated in vacuo. The residue was partitioned between ethyl acetate (˜50 ml) and water approximately 50 ml). The phases were separated and the aqueous phase washed with further ethyl acetate (2×approximately 30 ml). The combined organic layers were filtered through a hydrophobic frit and the filtrate concentrated in vacuo to give the crude material (0.64 g). The sample was loaded in dichloromethane and purified on silica 70 g using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and concentrated in vacuo to give the title compound as a colourless solid (342 mg); LCMS: (System 4) MH+=206, tRET=1.50 min.

1. temperaturethe stirred solution cooled in an ice-water bath
2. concentrationThe solvent was concentrated in vacuo
3. customThe residue was partitioned between ethyl acetate (˜50 ml) and water approximately 50 ml)
4. customThe phases were separated
5. washthe aqueous phase washed with further ethyl acetate (2×approximately 30 ml)
6. filtrationThe combined organic layers were filtered through a hydrophobic frit
7. concentrationthe filtrate concentrated in vacuo
8. customto give the crude material (0.64 g)
9. custompurified on silica 70 g
10. concentrationconcentrated in vacuo

ORD record

ord-280e9bb139544fefa7ed37b27a0a5169

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399436B2