Propionyl bromide → 5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-on

Participants

Role	Name	HCID	Charge
Reactant	Propionyl bromide	HCID 69018	—
Reactant	2-(5-Amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	HCID 19939462	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Product	5-n-Butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-on	HCID 19939418	65%

Reaction Steps

By the procedure of Example 69, 2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]-5'-ethylbiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step D) was reacted with propionyl bromide in the presence of DMAP. Purification of the crude product by flash chromatography on silica gel (gradient elution with 1-4% MeOH in CH2Cl2) afforded a 65% yield of the title compound as a cream-colored solid, mp 144°-146° C.; homogeneous by TLC in 9:1 CH2Cl2 --MeOH; m/e 734 (M+1)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05411980
Source dataset	uspto-grants-1995_05
ORD ID	ord-8e3ad536e2b044d0b3e1ff63c3a2902a
Source note	uspto-grants-1995_05