Реакция #1444738

Уравнение реакции

n-propylamine

2-amino-2-cyanoacetamide

ethyl 2-phenylethanimidoate hydrochloride

→

title compound

Выход 21.1%

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

Выход 21.1%

Растворители

acetonitrile

Условия реакции

Обработка

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

Методика

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%).

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