p-Fluorophenethylamine → N-(3-Amino-propyl)-N-(3-{2-[2-(4-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	p-Fluorophenethylamine	HCID 4653	—
Reactant	(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester	HCID 86603242	—
Product	N-(3-Amino-propyl)-N-(3-{2-[2-(4-fluoro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide	HCID 58603411	—

Reaction Steps

Intermediate 4 was coupled with 2-(4-fluoro-phenyl)-ethylamine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 458. 1H NMR (Varian 300 MHz, CDCl3-CD3OD, shifts relative to the solvent peak at 7.24 ppm) δ 8.1 (m, 3H) 7.7 (m, 1H) 7.5 (m, 2H) 7.2 (m, 2H) 6.9 (m, 2H) 4.5 (s, 2H) 3.8 (m, 2H) 3.7 (m, 1H) 3.4 (m, 2H) 2.9 (m, 7H) 1.9 (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-85d66937f53f46f5bfb1780335ba307c
Source note	uspto-grants-2012_09