2-(4-Chlorophenyl)ethylamine → N-(3-Amino-propyl)-N-(3-{2-[2-(4-chloro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	2-(4-Chlorophenyl)ethylamine	HCID 67430	—
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-chloro-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide	HCID 58603649	—

Reaction Steps

Intermediate 4 was coupled to 2-(4-chloro-phenyl)-ethylamine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 474. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.30 ppm) δ 8.7 (m, 1H) 8.16 (m, 4H) 7.65 (m, 6H) 4.45 (s, 2H) 3.95 (m, 2H) 3.4 (m, 2H) 3.18 (m, 4H) 3.0 (m, 2H) 2.9 (s, 3H) 1.75 (m, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-b032cb09dad649f7b4d3e5be67e918a7
Source note	uspto-grants-2012_09