4-(2-Aminoethyl)-2-chlorophenol → 2-Chloro-4-(2-{4-[3-(3,5-dimethyl-piperazin-1-ylmethyl)-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]-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester	HCID 86603325	—
Product	2-Chloro-4-(2-{4-[3-(3,5-dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol	HCID 58603641	—

Reaction Steps

Intermediate 142 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 452. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.63 (s, 1H) 8.35 (d, 2H)) 7.93 (d, 1H) 7.74 (d, 1H) 7.62 (d, 1H) 7.17 (s, 1H) 7.07 (d, 1H) 6.74 (d, 1H) 4.60 (s, 2H) 3.60-3.70 (m, 6H) 3.35 (t, 2H) 2.92 (t, 2H) 1.44 (d, 6H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-1d8539601470478982e6ec2a6fc62902
Source note	uspto-grants-2010_06