Tyramine → 4-{2-[4-(3-{[Ethyl-(2(S)-pyrrolidin-2-yl-ethyl)-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Participants

Role	Name	HCID	Charge
Reactant	Tyramine	HCID 5610	—
Reactant	2-(2-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester	HCID 86603300	—
Product	4-{2-[4-(3-{[Ethyl-(2(S)-pyrrolidin-2-yl-ethyl)-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol	HCID 58603420	—

Reaction Steps

Intermediate 107 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 447. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.62 (s, 1H), 8.37 (d, 1H), 8.34 (m, 1H), 7.93 (d, 1H), 7.72 (t, 1H), 7.66 (d, 1H), 7.11 (d, 2H), 6.67 (d, 2H), 4.52 (m, 2H), 3.95 (m, 2H), 3.58 (m, 2H), 3.27 (m, 4H), 2.93 (t, 2H), 2.24 (m, 4H), 1.99 (m, 2H), 1.70 (m, 1H), 1.40 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-6a4b3a8c6ec947f19a5dd3bd56e3cff9
Source note	uspto-grants-2010_06