Vanillylamine → N-(3-Amino-propyl)-N-{3-[2-(4-hydroxy-3-methoxy-benzylamino)-pyrimidin-4-yl]-benzyl}-methanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Vanillylamine	HCID 70966	—
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-(4-hydroxy-3-methoxy-benzylamino)-pyrimidin-4-yl]-benzyl}-methanesulfonamide	HCID 58603365	—

Reaction Steps

Intermediate 4 was coupled with 4-Aminomethyl-2-methoxy-phenol following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 472. 1H NMR (Varian 300 MHz, CDCl3-CD3OD, shifts relative to the solvent peak at 7.24 ppm) δ 8.2 (m, 3H) 7.6 (m, 2H) 7.3 (m, 2H) 6.8 (m, 2H) 4.4 (s, 2H) 3.8 (s, 2H) 3.7 (m, 2H) 3.4 (s, 3H) 2.9 (s, 3H) 2.8 (m, 2H) 1.7 (m, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-70af9677aefd4f3ea1364540efd1502b
Source note	uspto-grants-2012_09