2-(3,5-Difluorophenyl)ethan-1-amine → [2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(S),6(R)-dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine

Participants

Role	Name	HCID	Charge
Reactant	2-(3,5-Difluorophenyl)ethan-1-amine	HCID 3673665	—
Reactant	4-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester	HCID 86603308	—
Product	[2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(S),6(R)-dimethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine	HCID 58603503	—

Reaction Steps

Intermediate 114 was coupled with 2-(3,5-difluoro-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 439. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.57 (s, 1H), 8.36 (t, 2H), 7.94 (d, 1H), 7.74 (m, 2H), 6.99 (d, 2H), 6.75 (t, 1H), 3.77 (m, 5H), 3.64 (m, 5H), 3.07 (t, 2H), 1.69 (d, 6H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-e3ffa9518fc6415cab7221085d89eb64
Source note	uspto-grants-2012_09