Phenethylamine, m-trifluoromethyl- → (4-{3-[(Ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Participants

Role	Name	HCID	Charge
Reactant	Phenethylamine, m-trifluoromethyl-	HCID 104223	—
Reactant	4-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester	HCID 86603290	—
Product	(4-{3-[(Ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine	HCID 58603387	—

Reaction Steps

Intermediate 84 was coupled with 2-(3-trifluoromethyl-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 485. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.24 (m, 3H), 7.77 (t, 1H), 7.67 (t, 1H), 7.55 (m, 2H), 7.35 (m, 3H), 4.54 (s, 2H), 3.79 (m, 4H), 3.60 (d, 2H), 3.08 (m, 5H), 2.42 (d, 2H), 2.12 (m, 2H), 1.30 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-1fcb4d0f59b146ac9b450ce5565f3765
Source note	uspto-grants-2012_09