Reaktion #607883

Reaktionsgleichung

HCl

1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid

HOAT

EDCI

Et3N

2-amino-5-hydroxypyridine hydrochloride

Et3N

→

title compound

Ausbeute 78.4%

N-(5-hydroxypyridin-2-yl)-2,5-dimethyl-3-oxo-1-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Ausbeute 78.4%

Lösungsmittel

water

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at rt for 1 hour
2. 2
   workup.ADDITIONfollowed by the addition of the above prepared mixture
3. 3
   TemperaturThe reaction was heated at 60° C. for 5 hours
4. 4
   Temperaturcooled to rt
5. 5
   ExtraktionThe mixture was extracted with EtOAc (20 mL×4)
6. 6
   Waschenthe combined organic phases were washed with brine (20 mL)
7. 7
   Trocknendried over anhydrous Na2SO4
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Vorschrift

A suspension of 2-amino-5-hydroxypyridine hydrochloride (500 mg, 3.41 mmol) and Et3N (0.77 mL, 5.5 mmol) in DMF (8 mL) was stirred at rt for 1 hour. At the same time, to a solution of 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (0.64 g, 2.75 mmol), HOAT (449 mg, 3.3 mmol) and EDCI (0.63 g, 3.3 mmol) in DMF (8 mL) was added Et3N (0.77 mL, 5.5 mmol) drop wise. The mixture was stirred at rt for 1 hour, followed by the addition of the above prepared mixture. The reaction was heated at 60° C. for 5 hours, then cooled to rt and diluted with water (150 mL). and adjust to pH=6 with HCl (1 M). The mixture was extracted with EtOAc (20 mL×4), and the combined organic phases were washed with brine (20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the title compound as a pale yellow solid (699 mg, 78%).

Quelle