p-Bromophenethylamine → [2-(4-Bromo-phenyl)-ethyl]-(4-{3-[(3(S)-methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-yl)-amine

Participants

Role	Name	HCID	Charge
Reactant	p-Bromophenethylamine	HCID 533915	—
Reactant	4(R)-[3-(2-Chloro-pyrimidin-4-yl)-benzylamino]-3(S)-methyl-piperidine-1-carboxylic acid benzyl ester	HCID 86603319	—
Product	[2-(4-Bromo-phenyl)-ethyl]-(4-{3-[(3(S)-methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-yl)-amine	HCID 58603604	—

Reaction Steps

Intermediate 136 was coupled with 2-(4-bromo-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G3. LC-MS showed the product had the expected M+H+ of 481. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.67 (s, 1H) 8.39 (d, 2H) 7.95 (d, 1H)) 7.69 (t, 1H) 7.40 (d, 2H) 7.28 (d, 2H) 4.50 (s, 2H) 4.00 (m, 1H) 3.84 (m, 1H) 3.72 (m, 1H) 3.57 (m, 1H) 3.42 (d, 1H) 3.36 (d, 1H) 3.20 (t, 2H) 3.04 (t, 2H) 2.30 (m, 2H) 1.30 (d, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-ca8c246a4a274acd8c5d5e7eff49fc73
Source note	uspto-grants-2010_06