Reacción #159016

Ecuación de reacción

N-methylmorpholine

5-(6-Bromo-naphthalen-2-yl)-2-pyrrolidin-2-yl-1H-imidazole

2-methoxycarbonylamino-3-methyl-butyric acid

HATU

→

(1-{2-[5-(6-bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Rendimiento 72.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated under vacuum
2. 2
   workup.DISSOLUTIONThe oil was dissolved in dichloromethane
3. 3
   Otropurified by chromatography (0-100% ethyl acetate:hexanes)
4. 4
   Otroevaporated under vacuum

Procedimiento

5-(6-Bromo-naphthalen-2-yl)-2-pyrrolidin-2-yl-1H-imidazole (3.80 g), 2-methoxycarbonylamino-3-methyl-butyric acid (2.21 g), and HATU (5.06 g) were dissolved in anhydrous DMF (75 mL), and N-methylmorpholine (2.68 mL) was added. The reaction mixture was stirred at ambient temperature for 16 hours and evaporated under vacuum. The oil was dissolved in dichloromethane, purified by chromatography (0-100% ethyl acetate:hexanes), and evaporated under vacuum, giving (1-{2-[5-(6-bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (0.814 g, 72%) as an off-white solid.

Fuente