Reacción #821860

Ecuación de reacción

Et3N

product

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

5-amino-3-methylindazole

EDC

→

title compound

Rendimiento 6.0%

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

Rendimiento 6.0%

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 (20-100% EtOAc in Hexanes)
7. 7
   Otrofurther purified by reverse-phase HPLC (10-70% CH3CN/H2O—NH4OH to pH 10 over 20 minutes, retention time 11.74 min)

Procedimiento

The product of Example 5, Step 2 (225 mg, 0.75 mmol, 1.00 equiv), 5-amino-3-methylindazole (110 mg, 0.75 mmol, 1.0 equiv), and EDC (172 mg, 0.90 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.125 mL, 0.90 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. 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 (20-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (10-70% CH3CN/H2O—NH4OH to pH 10 over 20 minutes, retention time 11.74 min) to provide 18 mg (6%) of the title compound as a white solid. MS (ES+) m/e 429 [M+H]+

Fuente