Tyramine → N-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-ylmethyl-methanesulfonamide

HRID 2386396Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH:32]=[CH:31][N:30]=[C:29](Cl)[N:28]=3)[CH:22]=2)[S:16]([CH3:19])(=[O:18])=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.[NH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1>>[OH:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][CH2:35][NH:34][C:29]2[N:28]=[C:27]([C:23]3[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=3)[CH2:20][N:15]([CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[S:16]([CH3:19])(=[O:18])=[O:17])[CH:32]=[CH:31][N:30]=2)=[CH:38][CH:39]=1

Participants

Reactant 2

HCID 5610Tyramine

HCID 866032674-({[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59341048N-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-ylmethyl-methanesulfonamide

Procedure

Intermediate 34 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 496. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.3 (d, 2H), 8.1 (d, 1H) 7.6 (d, 1H) 7.5 (t, 1H), 7.3 (d, 1H), 7.1 (d, 2H), 6.7 (d, 2H), δ 4.5 (s, 2H), 3.3-3.2 (m, 6H), δ 3.0 (s, 3H), 2.9 (t, 2H), δ 2.7 (t, 2H), δ 1.6 (m, 1H), δ 1.2 (m, 4H).

Sources & evidence

ORD record: ord-0c2e45d4f46b428d82a5cd1231e41819
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268822B2

Reaction notes

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