4-(2-Aminoethyl)-2-chlorophenol → 4-{2-[4-(3-{[(3-Amino-propyl)-ethyl-amino]-methyl}-phenyl)-5-fluoro-pyrimidin-2-ylamino]-ethyl}-2-chloro-phenol

Participants

Role	Name	HCID	Charge
Reactant	4-(2-Aminoethyl)-2-chlorophenol	HCID 23071555	—
Reactant	(3-{[3-(2-Chloro-5-fluoro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-propyl)-carbamic acid tert-butyl ester	HCID 86603289	—
Product	4-{2-[4-(3-{[(3-Amino-propyl)-ethyl-amino]-methyl}-phenyl)-5-fluoro-pyrimidin-2-ylamino]-ethyl}-2-chloro-phenol	HCID 58603384	—

Reaction Steps

Intermediate 78 was coupled with 4-(2-amino-ethyl)-2-chloro-phenol following procedure Q. The resulting product was deprotected following procedure R. LC-MS showed the product had the expected M+H+ of 458. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.28 (d, 1H), 8.17 (s, 2H), 7.66 (m, 2H), 7.17 (d, 1H), 6.97 (d, 1H), 6.78 (d, 1H), 4.48 (s, 2H), 3.59 (t, 2H), 3.24 (m, 4H), 2.98 (t, 2H), 2.79 (t, 2H), 2.06 (m, 2H), 1.36 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-aaa849bd41f04b7798c1477e2b544c4b
Source note	uspto-grants-2012_09