Benzenemethanamine, 4-chloro-N-methyl- → N-(4-Chloro-benzyl)-2-(3,4-dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-N-methyl-butyramide

Participants

Role	Name	HCID	Charge
Reactant	Benzenemethanamine, 4-chloro-N-methyl-	HCID 66905	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	2-(3,4-Dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-butyric acid	HCID 57843537	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(4-Chloro-benzyl)-2-(3,4-dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-N-methyl-butyramide	HCID 25127969	67%

Reaction Steps

A mixture of 25 mg 2-(3,4-dichloro-phenyl)-4-(4-methanesulfonyl-piperazin-1-yl)-butyric acid (intermediate 1), 24.1 mg (0.075 mmol) TBTU, 11.67 mg (0.075 mmol) (4-chloro-benzyl)-methyl-amine (commercially available) and 0.06 mL N,N-diisopropyl ethylamine in 0.75 mL DMF was shaken at room temperature and subsequently subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 20.7 mg (67%) of the title compound as yellow viscous oil. MS(m/e): 534.2 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592345B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-b10a0871b43f41fc9bc67b86a493b4bd
Source note	uspto-grants-2009_09