Tyramine → 4-[2-(4-{3-[(3(S)-Methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

Participants

Role	Name	HCID	Charge
Reactant	Tyramine	HCID 5610	—
Reactant	4(R)-[3-(2-Chloro-pyrimidin-4-yl)-benzylamino]-3(S)-methyl-piperidine-1-carboxylic acid benzyl ester	HCID 86603319	—
Product	4-[2-(4-{3-[(3(S)-Methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol	HCID 58603657	—

Reaction Steps

Intermediate 136 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G3. LC-MS showed the product had the expected M+H+ of 418. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.63 (s, 1H) 8.36 (d, 2H) 7.95 (d, 1H) 7.75 (t, 1H) 7.67 (d, 1H) 7.15 (d, 2H) 6.71 (d, 2H) 4.50 (s, 2H) 3.96 (m, 1H) 3.80 (m, 1H) 3.72 (m, 1H) 3.56 (d, 1H) 3.34 (d, 1H) 3.20 (t, 2H) 2.96 (t, 2H) 2.80 (m, 1H) 2.38 (dd, 2H) 1.36 (d, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07732444B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-b076bb0e5f074d2c81d7e1e6afc41e82
Source note	uspto-grants-2010_06