Propionyl bromide → 5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Participants

Role	Name	HCID	Charge
Reactant	Propionyl bromide	HCID 69018	—
Reactant	2(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	HCID 10257760	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Product	5-n-Butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one	HCID 10439146	84%

Reaction Steps

Propionyl bromide was reacted with 2(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step C) in the presence of DMAP according to the procedure of Example 69. Flash chromatography of the crude product on silica gel (gradient elution with 3:1 to 1:1 hexane-EtOAc) gave an 84% yield of the title compound as a white solid, mp 103°-105° C.; homogeneous by TLC (1:1 hexane-EtOAc); mass spectrum (FAB) m/e 648 (M+Li)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05411980
Source dataset	uspto-grants-1995_05
ORD ID	ord-fbf413da9d3c4edcb5e7e91cd01def6c
Source note	uspto-grants-1995_05