Tyramine → 4-(2-{4-[3-(2-Ethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Participants

Role	Name	HCID	Charge
Reactant	Tyramine	HCID 5610	—
Reactant	4-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3-ethyl-piperazine-1-carboxylic acid tert-butyl ester	HCID 86603306	—
Product	4-(2-{4-[3-(2-Ethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol	HCID 58603521	—

Reaction Steps

Intermediate 130 was coupled with tyramine following procedure F. The product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 418. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.35 (s, 1H) 8.29 (d, 2H) 8. 7.81 (d, 1H) 7.68 (t, 1H) 7.49 (d, 1H) 7.2-7.2 (m, 3H) 6.68 (d, 2H) 4.8 (d, 1H) 4.17 (d, 1H) 3.85 (br s, 2H) 3.68 (d, 1H) 3.1-3.6 (m, 6H) 2.9 (t, 2H) 2.2 (m, 1H) 1.9 (m, 1H) 1.1 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-d64f0a3acc6745c0bf3570e24e58eef4
Source note	uspto-grants-2010_06