Reacción #821853

Ecuación de reacción

Et3N

product

4-[4-(Trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

1H-indazol-5-amine

EDC

→

title compound

Rendimiento 33.0%

N-1H-Indazol-5-yl-2-methyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxamide

Rendimiento 33.0%

Disolventes

EtOAc

HCl

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe phases were separated
2. 2
   Lavadothe organic phase was washed twice with 1N HCl, once with satd
3. 3
   SecadoThe organic phase was dried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated en vacuo
6. 6
   OtroThe residue was purified by flash chromatography (100% EtOAc)

Procedimiento

The product of step 2 (146 mg, 0.512 mmol, 1.00 equiv), 1H-indazol-5-amine (68 mg, 0.512 mmol, 1.00 equiv) and EDC (118 mg, 0.615 mmol, 1.20 equiv) were suspended in 8.0 mL DMF. Et3N (0.086 mL, 0.615 mmol, 1.20 equiv) was added and the solution was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (100% EtOAc) to provide 0.070 g (33%) of the title compound as a white solid. MS (ES+) m/e 415 [M+H]+

Fuente