2-(3-Fluorophenyl)ethanamine → (4-{3-[(Ethyl-piperidin-3(S)-ylmethyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3-fluoro-phenyl)-ethyl]-amine

Participants

Role	Name	HCID	Charge
Reactant	2-(3-Fluorophenyl)ethanamine	HCID 533928	—
Reactant	3-({[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester	HCID 86603297	—
Product	(4-{3-[(Ethyl-piperidin-3(S)-ylmethyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-[2-(3-fluoro-phenyl)-ethyl]-amine	HCID 58603558	—

Reaction Steps

Intermediate 95 was coupled with 2-(3-fluoro-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 449. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.71 (s, 1H), 8.36 (t, 2H), 7.96 (d, 1H), 7.70 (m, 2H), 7.30 (s, 1H), 7.12 (d, 2H), 6.91 (s, 1H), 4.60 (s, 2H), 3.99 (s, 2H), 3.06 (m, 6H), 2.84 (m, 2H), 2.65 (t, 1H), 2.34 (m, 2H), 1.87 (m, 4H), 1.45 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-f396231134fe4fe2bd2a8f386e5f10c9
Source note	uspto-grants-2010_06