4-(2-Aminoethyl)-2-chlorophenol → 2-Chloro-4-(2-{4-[3-(2-piperidin-4-yl-ethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Participants

Role	Name	HCID	Charge
Reactant	4-(2-Aminoethyl)-2-chlorophenol	HCID 23071555	—
Reactant	4-{2-[3-(2-Chloro-pyrimidin-4-yl)-phenyl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester	HCID 86603296	—
Product	2-Chloro-4-(2-{4-[3-(2-piperidin-4-yl-ethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol	HCID 58603487	—

Reaction Steps

Intermediate 94 was coupled with 4-(2-amino-ethyl)-2-chloro-phenol following procedure Q. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 437. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.27 (d, 1H), 8.05 (s, 1H), 7.99 (m, 1H), 7.46 (d, 2H), 7.35 (d, 1H), 7.24 (d, 1H), 7.03 (d, 1H), 6.80 (d, 1H), 3.70 (m, 2H), 3.35 (m, 2H), 2.78 (m, 6H), 1.99 (d, 2H), 1.66 (m, 3H), 1.37 (m, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-263f315ba0954cf7b1b3cdcc85a570a8
Source note	uspto-grants-2010_06