Reaktion #607851

Reaktionsgleichung

4-(4-amino-2,3-difluorophenoxy)picolinamide

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

EDCI

HOAT

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

→

title compound

Ausbeute 33.2%

4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2,3-difluorophenoxy)picolinamide

Ausbeute 33.2%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was further stirred at 45° C. for 5 hours
2. 2
   TemperaturThe mixture was cooled to rt
3. 3
   Sonstigequenched with 5 mL of water
4. 4
   Extraktionextracted with EtOAc (10 mL×3)
5. 5
   WaschenThe combined organic phases were washed with brine (10 mL×3)
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by a silica gel column chromatography (EtOAc 100%)

Vorschrift

To a suspension of 4-(4-amino-2,3-difluorophenoxy)picolinamide (180 mg, 0.68 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (161 mg, 0.69 mmol) in DCM (4 mL) was added EDCI (157 mg, 0.82 mmol) and HOAT (19 mg, 0.14 mmol). The mixture was stirred at 45° C. for 12 hours, then more 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (87 mg, 0.37 mmol) was added and the reaction was further stirred at 45° C. for 5 hours. The mixture was cooled to rt, quenched with 5 mL of water, and extracted with EtOAc (10 mL×3). The combined organic phases were washed with brine (10 mL×3), dried over Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc 100%) to give the title compound as an orange solid (108 mg, 33.2%).

Quelle