Tyramine → N-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-ylmethyl-methanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Tyramine	HCID 5610	—
Reactant	4-({[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester	HCID 86603267	—
Product	N-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-ylmethyl-methanesulfonamide	HCID 59341048	—

Reaction Steps

Intermediate 34 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 496. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.3 (d, 2H), 8.1 (d, 1H) 7.6 (d, 1H) 7.5 (t, 1H), 7.3 (d, 1H), 7.1 (d, 2H), 6.7 (d, 2H), δ 4.5 (s, 2H), 3.3-3.2 (m, 6H), δ 3.0 (s, 3H), 2.9 (t, 2H), δ 2.7 (t, 2H), δ 1.6 (m, 1H), δ 1.2 (m, 4H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-0c2e45d4f46b428d82a5cd1231e41819
Source note	uspto-grants-2012_09