Reacción #1854226

Ecuación de reacción

bromomethylketone

2-Bromo-1-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-ethanone

1,1-dimethylethyl (3-amino-3-thioxopropyl)carbamate

sodium bicarbonate

→

1,1-dimethylethyl (2-(4-[6-(methoxy)-1,5-naphthyridin-4-yl]-1,3-thiazol-2-yl}ethyl)carbamate

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux for 1 hour under argon
3. 3
   OtroThe mixture was evaporated
4. 4
   Otrothe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
5. 5
   ExtracciónThe organic extract
6. 6
   Lavadowas washed with brine
7. 7
   Otrodried
8. 8
   Otroevaporated
9. 9
   OtroThe residue was chromatographed on silica eluting with a gradient of 0–50% ethyl acetate in dichloromethane affording a yellow solid (0.93 g, 26%)

Procedimiento

A mixture of bromomethylketone (b) (2.07 g, 9 mmol), 1,1-dimethylethyl (3-amino-3-thioxopropyl)carbamate (1.84 g, 9 mmol) and sodium bicarbonate (0.76 g, 9 mmol) in ethanol (120 mL) was heated to reflux for 1 hour under argon. The mixture was evaporated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic extract was washed with brine, dried and evaporated. The residue was chromatographed on silica eluting with a gradient of 0–50% ethyl acetate in dichloromethane affording a yellow solid (0.93 g, 26%).

Fuente