Reaktion #60039

Reaktionsgleichung

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

Ausbeute 83.0%

Lösungsmittel

NMP

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeUpon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml)
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with water (2×50 ml), brine (50 ml), dried Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe product was purified by flash chromatography
7. 7
   Wascheneluting with 10% methanol in dichloromethane
8. 8
   Sonstigedrying in vacuo

Vorschrift

4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile (6 M) in NMP (5 ml) was added to a stirred mixture of N-[2-(amidinoamino)ethyl](tert-butoxy)carboxamide, hydrochloride (3 M) and Cs2CO3 (2.4) 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, (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide was obtained as a dark red glass in 83% yield.

Quelle