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

Participants

Role	Name	HCID	Charge
Reactant	4-(2-Aminoethyl)-2-chlorophenol	HCID 23071555	—
Reactant	4-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-piperidine-1-carboxylic acid tert-butyl ester	HCID 86603290	—
Product	2-Chloro-4-[2-(4-{3-[(ethyl-piperidin-4-yl-amino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol	HCID 58603439	—

Reaction Steps

Intermediate 84 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 467. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.27 (m, 2H), 7.69 (m, 2H), 7.26 (d, 1H), 7.19 (m, 1H), 7.04 (s, 1H), 7.01 (d, 1H), 6.80 (d, 1H), 4.48 (m, 2H), 3.53 (m, 4H), 3.09 (m, 4H), 2.85 (t, 2H), 2.39 (d, 2H), 2.03 (m, 3H), 1.32 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-fd0694ce9fe043ddb3326ef668a45f37
Source note	uspto-grants-2010_06