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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 14886Generated: October 30, 2026

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

https://huagongshe.com/reaction/14886

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTyramineHCID 5610—
Reactant4-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2-(1H-indol-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl esterHCID 86603303—
Product4-[2-(4-{3-[3(S)-(1H-Indol-3-ylmethyl)-piperazin-1-ylmethyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenolHCID 58603773—

Reaction Steps

Intermediate 109 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 520. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.51 (s, 1H), 8.29 (d, 2H), 7.81 (d, 1H), 7.55 (m, 3H), 7.34 (d, 1H), 7.25 (s, 1H), 7.02 (m, 4H), 6.69 (s, 2H), 4.54 (m, 2H), 4.08 (m, 1H), 3.90 (m, 2H), 3.61 (m, 4H), 3.25 (m, 4H), 2.92 (t, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07732444B2
Source datasetuspto-grants-2010_06
ORD IDord-b86592ad3523402ab03c6d0328b0ca81
Source noteuspto-grants-2010_06