Reacción #60037

Ecuación de reacción

4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile

N-[2-(amidinoamino)ethyl](tert-butoxy)carboxamide, hydrochloride

Cs2CO3

→

(tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide

Rendimiento 83.0%

Disolventes

NMP

NMP

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroUpon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml)
2. 2
   OtroThe organic layer was separated
3. 3
   Lavadowashed with water (2×50 ml), brine (50 ml), dried Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe product was purified by flash chromatography
7. 7
   Lavadoeluting with 10% methanol in dichloromethane
8. 8
   Otrodrying in vacuo

Procedimiento

4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile (8.0 g, 30.0 mmol) in NMP (5 ml) was added to a stirred mixture of N-[2-(amidinoamino)ethyl](tert-butoxy)carboxamide, hydrochloride (13.8 g, 45 mmol)) and Cs2CO3 (11.72, 36.0 mmol) in NMP (15 ml). The reaction was heated to 100° C. for 48 hours. The reaction was followed by HPLC. Upon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml). The organic layer was separated and washed with water (2×50 ml), brine (50 ml), dried Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography eluting with 10% methanol in dichloromethane. After stripping off the solvents and drying in vacuo, 10.08 g of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide was obtained as a dark red glass in 83% yield.

Fuente