2-(6-fluoro-1H-indol-3-yl)ethanamine → N-(3-Amino-propyl)-N-(3-{2-[2-(6-fluoro-1H-indol-3-yl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	2-(6-fluoro-1H-indol-3-yl)ethanamine	HCID 854024	—
Reactant	(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester	HCID 86603242	—
Product	N-(3-Amino-propyl)-N-(3-{2-[2-(6-fluoro-1H-indol-3-yl)-ethylamino]-pyrimidin-4-yl}-benzyl)-methanesulfonamide	HCID 58603389	—

Reaction Steps

Intermediate 4 was coupled with 2-(6-Fluoro-1H-indol-3-yl)-ethylamine following procedure F and the resulting product deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 497. 1H NMR (Varian 300 MHz, CDCl3-CD3OD, shifts relative to the solvent peak at 7.24 ppm) δ 8.1 (m, 2H) 7.8 (d, 1H) 7.5 (m, 4H) 7.3 (m, 1H) 6.8 (m, 2H) 4.4 (d, 2H) 3.9 (m, 1H) 3.6 (m, 2H) 3.3 (m, 2H) 3.1 (m, 1H) 2.8 (m, 5H) 1.7 (m, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-a1fc96e1c21148c991f81cd1d511f27c
Source note	uspto-grants-2012_09