Reaktion #85381

Reaktionsgleichung

3-Chloro-N-ethyl-1-(pyridine-3-yl)-1H-pyrazol-amine

Carbonyldiimidazole

1H-imidazole hydrochloride

3-((3,3,3-trifluropropyl)thio)propanoic acid

→

solid

Ausbeute 86.5%

N-(3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide

Ausbeute 86.5%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred at 75° C. for 42 hours, at which point HPLC analysis
2. 2
   TemperaturThe reaction was cooled to 20° C.
3. 3
   Einengenconcentrated to dryness
4. 4
   SonstigeThe residue was purified by flash column chromatography
5. 5
   Einengenconcentrated

Vorschrift

A 20 mL vial was charged with 3-((3,3,3-trifluropropyl)thio)propanoic acid (0.999 g, 4.94 mmol) and acetonitrile (5 mL). Carbonyldiimidazole (0.947 g, 5.84 mmol) (off-gassing) and 1H-imidazole hydrochloride (0.563 g, 5.39 mmol) were added and the reaction was stirred at 20° C. for 4 hours. 3-Chloro-N-ethyl-1-(pyridine-3-yl)-1H-pyrazol-amine (1.00 g, 4.49 mmol) was added and the reaction was stirred at 75° C. for 42 hours, at which point HPLC analysis indicated that the conversion was 96%. The reaction was cooled to 20° C. and concentrated to dryness. The residue was purified by flash column chromatography using 80% ethyl acetate/hexanes as eluent. Pure fractions were combined and concentrated to afford a light yellow solid (1.58 g, 86%).

Quelle