Réaction #64533

Équation de réaction

2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

propyl isocyanate

→

desired compound

Rendement 61.0%

5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2-[2-chloro-5-(N3 -propylureido)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Rendement 61.0%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   AutreAfter quenching with water
2. 2
   Extractionthe organic material was extracted with EtOAc
3. 3
   Lavagewashed with water and brine
4. 4
   Séchagedried over sodium sulfate
5. 5
   AutreThe crude product obtained
6. 6
   Filtrationafter filtration and removal of volatiles
7. 7
   Autrechromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2)

Mode opératoire

At room temperature, under N2, a solution of 34 mg (0.052 mmole) of 2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 60), 6.4 mg (0.052 mmole) of DMAP, 23 mg (0.26 mmole) of propyl isocyanate, and 1 mL of pyridine was stirred overnight. After quenching with water, the organic material was extracted with EtOAc, washed with water and brine, and dried over sodium sulfate. The crude product obtained after filtration and removal of volatiles was flash chromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2) to give 23 mg (61%) of the desired compound as a white solid, mp >208° C. (gradual), homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 773 (M+K)+.

Source