Tyramine → N-(3-{5-Fluoro-2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-yl-methanesulfonamide

HRID 14849Notes

Reaction equation

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

Participants

Reactant 2

HCID 5610Tyramine

HCID 866032884-{[3-(2-Chloro-5-fluoro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603546N-(3-{5-Fluoro-2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzyl)-N-piperidin-4-yl-methanesulfonamide

Procedure

Intermediate 77 was coupled with tyramine following procedure Q. The resulting product was deprotected following procedure R. LC-MS showed the product had the expected M+H+ of 500. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.23 (d, 1H), 8.16 (s, 1H), 7.96 (d, 1H), 7.48 (m, 2H), 7.05 (d, 2H), 6.69 (d, 2H), 4.54 (s, 2H), 3.90 (m, 1H), 3.56 (t, 2H), 3.34 (m, 2H), 3.00 (s, 3H), 2.91 (m, 2H), 2.80 (t, 2H), 1.84 (m, 4H).

Sources & evidence

ORD record: ord-9e24b1e7502e451d99ddacbeae6fca0e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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