2-(3,5-Difluorophenyl)ethan-1-amine → [2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(S)-ethyl-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-ethyl-piperazine-1-carboxylic acid tert-butyl ester	HCID 86603306	—
Product	[2-(3,5-Difluoro-phenyl)-ethyl]-{4-[3-(2(S)-ethyl-piperazin-1-ylmethyl)-phenyl]-pyrimidin-2-yl}-amine	HCID 58603775	—

Reaction Steps

Intermediate 112 was coupled with 2-(3,5-difluoro-phenyl)-ethylamine following procedure F. The enantiomers of this product were separated by chiral HPLC, with compound 195 coming from the first peak to elute. 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 8.74 (s, 1H), 8.38 (d, 2H), 7.97 (d, 1H), 7.71 (m, 2H), 7.00 (d, 2H), 6.74 (s, 1H), 4.58 (m, 6H), 4.07 (m, 4H), 3.25 (m, 3H), 3.07 (t, 2H), 1.39 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-aad9c1b036034706a823acc04a751e5e
Source note	uspto-grants-2010_06