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

HRID 14833Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][N:14]([C:29](=[O:31])[CH3:30])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:17]=2)[CH2:9]1)=O)(C)(C)C.[NH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1>>[OH:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][CH2:33][NH:32][C:24]2[N:23]=[C:22]([C:18]3[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=3)[CH2:15][N:14]([CH2:13][CH:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)[C:29](=[O:31])[CH3:30])[CH:27]=[CH:26][N:25]=2)=[CH:36][CH:37]=1

Participants

Reactant 2

HCID 5610Tyramine

HCID 866032803-({Acetyl-[3-(2-chloro-pyrimidin-4-yl)-benzyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603456N-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-pyrrolidin-3-ylmethyl-acetamide

Procedure

Intermediate 60 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 446.

Sources & evidence

ORD record: ord-1a564b98575c42958d69f0560995ccbf
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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