Réaction #51644

Équation de réaction

2-Furancarboxylic acid

carbonyldiimidazole

2-{(1S)-1-Amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole

→

expected product

Rendement 94.0%

2-{(1S)-1-[(2-Furanyl)carbonylamino]-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole

Rendement 94.0%

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAminomethylated resin was then added (50-60 mg, 1.2 mmol/g, Novabiochem) in order
2. 2
   Autreto quench the excess
3. 3
   Autrefor about 12 hours
4. 4
   AutrePurification on silica gel pad (200 mg, Alltech) with ethyl acetate as eluent

Mode opératoire

2-Furancarboxylic acid (12.6 mg, 0.11 mmol) was activated overnight at about 22° C. with carbonyldiimidazole (0.11 mmol, 0.2M in chloroform). 2-{(1S)-1-Amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole (0.1 mmol, 0.5M in chloroform) was added to the media and the mixture was stirred for about 12 hours at about 22° C. Aminomethylated resin was then added (50-60 mg, 1.2 mmol/g, Novabiochem) in order to quench the excess of acylating agent for about 12 hours. Purification on silica gel pad (200 mg, Alltech) with ethyl acetate as eluent gave the expected product (37.2 mg, 94%). 1H-NMR (CDCl3, 100 MHz) δ: 8.36 (br s, 1H); 7.67-6.4 (m, 16H); 5.48 (qd, J=7.1 Hz, 1H); 3.6 (ABX system, 2H). LC/MS: m/z=397 (M+H).

Source