Reacción #71337

Ecuación de reacción

8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-amide

HCl

Na2CO3

→

title compound

Rendimiento 79.1%

8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (1H-imidazol-2-yl)-amide

Rendimiento 79.1%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to rt
2. 2
   Extracciónextracted with DCM
3. 3
   LavadoThe combined organic phase was washed with H2O and brine
4. 4
   Secadodried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Procedimiento

A mixture of 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-amide (Step 14.1) (0.527 g, 0.82 mmol), 5 N HCl (7 mL), and EtOH (4 mL) was stirred at 65° C. for 10 h. The reaction mixture was allowed to cool to rt, basified by addition of a saturated aqueous solution of Na2CO3, and extracted with DCM. The combined organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) to afford 0.288 g of the title compound as a yellow solid: ESI-MS: 443.9/445.9 [M+H]+; tR=3.74 min (System 1); TLC: Rf=0.30 (DCM/MeOH/NH3aq, 94:5:1).

Fuente