Tyramine → 1-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-piperazine-2-carbonitrile

HRID 14945Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[CH:10]([C:28]#[N:29])[CH2:9]1)=O)(C)(C)C.[NH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1>>[OH:39][C:36]1[CH:37]=[CH:38][C:33]([CH2:32][CH2:31][NH:30][C:23]2[N:22]=[C:21]([C:17]3[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=3)[CH2:14][N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]3[C:28]#[N:29])[CH:26]=[CH:25][N:24]=2)=[CH:34][CH:35]=1

Participants

Reactant 2

HCID 5610Tyramine

HCID 86603322HCID 86603322, compound

Product 1

HCID 670456231-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-piperazine-2-carbonitrile

Procedure

Intermediate 139 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+−CN of 388. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.32 (d, 1H) 8.27 (s, 1H) 8.23 (d, 1H) 7.75 (d, 1H) 7.62 (t, 1H) 7.55 (d, 1H) 7.14 (d, 2H) 6.71 (d, 2H) 4.38 (s, 2H) 3.92 (dd, 1H) 3.80 (d, 2H) 3.40 (t, 2H) 3.24 (t, 2H) 2.95 (t, 2H) 2.84 (t, 2H).

Sources & evidence

ORD record: ord-171083ccf2ce4b4180735780a90193f9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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