Tyramine → 4-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 14734

Reaction equation

HRID 14734 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH: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)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=4)[N:22]=3)[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 5610TyramineHCID 866032444-[3-(2-Chloro-pyrimidin-4-yl)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586034184-(3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

Procedure

Intermediate 7 was coupled with tyramine following procedure F. LC-MS showed the product had the expected M+H+ of 490. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.28 (d, 1H) 7.25 (m, 3H) 7.05 (m, 2H) 6.92 (d, 1H) 6.7 (m, 3H) 5.45 (m, 1H) 4.0 (m, 2H) 3.7 (m, 4H) 3.49 (m, 1H) 2.85 (m, 4H) 2.45 (t, 2H) 1.5 (s, 9H).

Sources & evidence

ORD record
ord-a870d7e28d764405b07914de9c55f581
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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