Triethylamine → HCID 178522345, compound

To a solution of 1H-pyrazol-3-amine (160 mg, 1.93 mmol, Fluka) in acetonitrile (10 ml) was added triethylamine (0.537 ml, 3.85 mmol, Aldrich) and the stirred solution cooled in an ice-water bath. A solution of 2,6-dichlorobenzoyl chloride (0.276 ml, 1.926 mmol, Aldrich) in acetonitrile (5 ml) was added dropwise. The mixture was stirred under nitrogen and allowed to warm slowly to ambient temperature overnight. The mixture was concentrated in vacuo. The residue was partitioned between DCM (20 ml) and water (20 ml). Insoluble material precipitated. The layers were separated and the aqueous phase then extracted with ethyl acetate (approximately 50 ml). The combined organic layers were filtered through a hydrophobic frit and concentrated in vacuo to give the crude material as an off-white foam. The residue was dissolved in methanol and adsorbed onto fluorosil. The sample was purified on silica 50 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 (0.303 g).

1. temperaturethe stirred solution cooled in an ice-water bath
2. concentrationThe mixture was concentrated in vacuo
3. customThe residue was partitioned between DCM (20 ml) and water (20 ml)
4. customInsoluble material precipitated
5. customThe layers were separated
6. extractionthe aqueous phase then extracted with ethyl acetate (approximately 50 ml)
7. filtrationThe combined organic layers were filtered through a hydrophobic frit
8. concentrationconcentrated in vacuo
9. customto give the crude material as an off-white foam
10. customThe sample was purified on silica 50 g
11. concentrationconcentrated in vacuo

ORD record

ord-76aa5022450c4f0e855acf8a0963068f

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399436B2