Reaktion #1442739

Reaktionsgleichung

n-propylamine

2-amino-2-cyanoacetamide

ethyl 2-phenylethanimidoate hydrochloride

→

title compound

Ausbeute 21.1%

5-Amino-2-benzyl-1-n-propylimidazole-4-carboxamide

Ausbeute 21.1%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice-bath
2. 2
   FiltrationThe resulting precipitate was filtered off
3. 3
   workup.STIRRINGthe solution stirred at room temperature for 72 hours
4. 4
   EinengenThe reaction mixture was concentrated under reduced pressure
5. 5
   Sonstigethe residue purified by column chromatography on silica gel

Vorschrift

A solution of 2-amino-2-cyanoacetamide (prepared as described in WO 94/00453; 250 mg, 2.5 mmol) in acetonitrile (6 mL) was added to ethyl 2-phenylethanimidoate hydrochloride (prepared as described in J. Med. Chem. 38 (18), 3676 (1995); 500 mg, 2.5 mmol), and the suspension stirred at room temperature for an hour, then cooled in an ice-bath. The resulting precipitate was filtered off, n-propylamine (160 μL, 2.5 mmol) added to the filtrate and the solution stirred at room temperature for 72 hours. The reaction mixture was concentrated under reduced pressure, and the residue purified by column chromatography on silica gel using dichloromethane:methanol (95:5) as eluant to afford the title compound as a tan coloured solid (136 mg, 21%).

Quelle