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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 14800Generated: October 27, 2026

Tyramine → 3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/14800

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTyramineHCID 5610—
Reactant3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86603269—
Product3-[(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonyl-amino]-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 67044832—

Reaction Steps

Intermediate 36 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 468. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.2 (d, 2H), 8.0 (d, 1H) 7.6 (d, 1H) 7.5 (t, 1H), 7.2 (d, 1H), 7.1 (d, 2H), 6.7 (d, 2H), δ 4.6 (s, 2H), 3.5-3.4 (m, 6H), δ 3.2-3.1 (m, 1H), 3.0 (s, 3H), δ 2.9 (t, 2H), δ 2.2-2.0 (m, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07732444B2
Source datasetuspto-grants-2010_06
ORD IDord-9b33ea4eaa154d628ade6bb36aaef07a
Source noteuspto-grants-2010_06