Réaction #52274

Équation de réaction

3-[5-(2-aminooxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester

1H-pyrazole-1-carboxamide hydrochloride

→

title compound

Rendement 97.0%

3-(5-{2-[Guanidino-oxy]-ethoxy}-indol-1-yl)-3-phenyl-propionic acid ethyl ester

Rendement 97.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was evaporated under vacuum
2. 2
   Autrethe crude mixture was purified via column chromatography with silica gel
3. 3
   Lavageeluting with 10% methanol/dichloromethane

Mode opératoire

3-[5-(2-aminooxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester (0.28 g, 0.75 mmol) and 1H-pyrazole-1-carboxamide hydrochloride (0.99 g, 0.67 mmol) were dissolved in methanol (3 mL) and stirred for 5 days. The solvent was evaporated under vacuum and the crude mixture was purified via column chromatography with silica gel, eluting with 10% methanol/dichloromethane to afford the title compound (97% yield). 1H NMR (CDCl3), δ 7.11-7.26 (m, 7H), 7.00 (d, 1H, J=2.3 Hz), 6.75 (dd, 1H, J=2.3, 8.8 Hz), 6.43 (d, 1H, J=3.2 Hz), 5.98 (t, 1H, J=7.6 Hz), 4.08 (m, 2H), 3.99 (m, 4H), 3.23 (m, 2H), 1.05 (t, 3H, J=7.2 Hz).

Source