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

Participants

Role	Name	HCID	Charge
Reactant	Thiopheneethanamine	HCID 116521	—
Reactant	3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-azetidine-1-carboxylic acid tert-butyl ester	HCID 86603299	—
Product	(4-{3-[(Ethyl-piperidin-3(S)-ylmethyl-amino)-methyl]-phenyl}-pyrimidin-2-yl)-(2-thiophen-2-yl-ethyl)-amine	HCID 58603419	—

Reaction Steps

Intermediate 105 was coupled with 2-thiophen-2-yl-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 437. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.71 (s, 1H), 8.40 (d, 2H), 7.98 (d, 1H), 7.75 (s, 2H), 7.21 (d, 1H), 6.93 (d, 2H), 4.61 (s, 2H), 4.03 (s, 2H), 3.13 (m, 6H), 2.85 (t, 2H), 2.67 (t, 1H), 2.39 (m, 2H), 1.81 (m, 4H), 1.29 (t, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268822B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-3da0c766e9984e3b9051f594d73901fa
Source note	uspto-grants-2012_09