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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2386557Generated: October 27, 2026

4-(2-Aminoethyl)-2-chlorophenol → 2-Chloro-4-(2-{4-[3-(2,5-diaza-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

https://huagongshe.com/reaction/2386557

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-(2-Aminoethyl)-2-chlorophenolHCID 23071555—
Reactant5-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl esterHCID 86603326—
Product2-Chloro-4-(2-{4-[3-(2,5-diaza-bicyclo[2.2.1]hept-2-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenolHCID 58603729—

Reaction Steps

Intermediate 143 was coupled with 4-(2-amino-ethyl)-2-chloro-phenol following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 436. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.38 (s, 1H) 8.26 (d, 2H) 7.87 (d, 1H) 7.72 (m, 1H) 7.48 (d, 1H) 7.20 (s, 1H) 7.00 (d, 1H) 6.79 (d, 1H) 4.62 (s, 2H) 3.92 (d, 2H) 3.74 (d, 2H) 3.61 (t, 2H) 3.24 (t, 2H) 2.88 (t, 2H) 2.76 (d, 1H) 2.37 (d, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08268822B2
Source datasetuspto-grants-2012_09
ORD IDord-eabd3960e8f54965b9a4b31829e924fd
Source noteuspto-grants-2012_09