2-(3,5-Difluorophenyl)ethan-1-amine → [2-(3,5-Difluoro-phenyl)-ethyl]-(4-{3-[3(S)-(1H-indol-3-ylmethyl)-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]-2-(1H-indol-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester	HCID 86603303	—
Product	[2-(3,5-Difluoro-phenyl)-ethyl]-(4-{3-[3(S)-(1H-indol-3-ylmethyl)-piperazin-1-ylmethyl]-phenyl}-pyrimidin-2-yl)-amine	HCID 58603671	—

Reaction Steps

Intermediate 109 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 540. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.59 (s, 1H), 8.34 (d, 1H), 8.29 (d, 1H), 7.84 (d, 1H), 7.60 (m, 3H), 7.33 (d, 1H), 7.26 (s, 1H), 6.98 (m, 4H), 6.72 (s, 1H), 4.63 (s, 2H), 4.16 (m, 1H), 4.04 (s, 2H), 3.49 (m, 4H), 3.26 (m, 4H), 3.05 (t, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-6c163847b9144d87b3e1406f9a64e3b8
Source note	uspto-grants-2010_06