1-Hydroxybenzotriazole → 6-Methyl-4'-trifluoromethyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	[1,1'-Biphenyl]-2-carboxylic acid, 6-methyl-4'-(trifluoromethyl)-	HCID 10945826	—
Reactant	4-[4-(3-Cyano-benzyl)-piperazin-1-yl]-phenylamine	HCID 11185447	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Triethylamine	HCID 8471	—
Product	6-Methyl-4'-trifluoromethyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide	HCID 9872372	16.1%

Reaction Steps

To a stirred solution of 4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenylamine (400 mg), 6-methyl-4′-trifluoromethyl-biphenyl-2-carboxylic acid (460 mg), HOBt (222 mg), and Et3N (166 mg) in CH2Cl2 (20 mL) was added at room temperature EDCl (315 mg) and the mixture was stirred at room temperature for 16 hours. The organic solution was then washed with water, with a saturated solution of NaHCO3 and dried over Na2SO4. After filtration and evaporation of the filtrate, the residue was purified by flash chromatography eluting with CH2Cl2/MeOH (98/2) and crystallized from AcOEt to give the title compound (122 mg) as white crystals.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06552022B1
Source dataset	uspto-grants-2003_04
ORD ID	ord-3d60cce481a34cd4aa673a494393cd2e
Source note	uspto-grants-2003_04