4-Fluorobenzylamine → 2-(4-Fluoro-benzylamino)-N-[3-(2-pyrrolidin-1-yl-ethoxy)-4-trifluoromethyl-phenyl]-nicotinamide

Participants

Role	Name	HCID	Charge
Reactant	4-Fluorobenzylamine	HCID 67326	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Chloro-N-[3-(2-pyrrolidin-1-yl-ethoxy)-4-trifluoromethyl-phenyl]-nicotinamide	HCID 21959348	—
Solvent	Diethyl Ether	HCID 3283	—
Product	2-(4-Fluoro-benzylamino)-N-[3-(2-pyrrolidin-1-yl-ethoxy)-4-trifluoromethyl-phenyl]-nicotinamide	HCID 10164071	—

Reaction Conditions

Temperature	130 °C

Reaction Steps

2-Chloro-N-[3-(2-pyrrolidin-1-yl-ethoxy)-4-trifluoromethyl-phenyl]-nicotinamide (199.1 mg), DIEA (252 μL) and 4-fluorobenzylamine (193 μL) were combined in a sealed tube and heated to 130° C. for 2 h. The mixture was purified on silica gel chromatography (2-3.5% MeOH/CH2Cl2). The desired fractions were concentrated in vacuo, and the residue was dissolved in Et2O and hexanes were added until the solution became cloudy. The solids were filtered, and dried. Additional material was obtained from the filtrate upon additional rounds of concentration, dissolving in Et2O and treatment with hexanes. M+H 503.4, Calc'd for C26H26N4O2F4-502.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07101868B2
Source dataset	uspto-grants-2006_09
ORD ID	ord-8609d89a78df4d209957136985cb35c5
Source note	uspto-grants-2006_09