Reacción #156764

Ecuación de reacción

(cyanomethyl)trimethylphosphonium iodide

(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

ethyl 6-(piperazin-1-yl)nicotinate

DIPEA

→

title compounds

Rendimiento 77.0%

(S)-ethyl 6-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)nicotinate

Rendimiento 77.0%

Disolventes

K2CO3

water

propionitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled
2. 2
   Extracciónextracted with dichloromethane (2×10 mL)
3. 3
   SecadoThe combined organic extracts were dried (MgSO4)
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe resulting oil was crystallized with ethyl ether-ethanol (10:1, 22 mL)

Procedimiento

(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (233 mg, 1.06 mmol), ethyl 6-(piperazin-1-yl)nicotinate (270 mg, 0.1.15 mmol), DIPEA (0.80 mL), and (cyanomethyl)trimethylphosphonium iodide (369 mg, 01.82 mmol) were suspended in propionitrile (3 mL) and heated in a closed vial at 90° C. for 5 h. The mixture was cooled, diluted with a solution of K2CO3 (2.50 g) in water (15 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The resulting oil was crystallized with ethyl ether-ethanol (10:1, 22 mL) to afford the title compounds as a tan solid (0.355 mg, 77%). [M+H] calc'd for C23H28N6O3, 437; found, 437.

Fuente