3-Methoxytyramine → (4-{2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-carbamic acid benzyl ester

HRID 14817

Reaction equation

HRID 14817 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][N:20]=[C:19](Cl)[N:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([O:35][CH3:36])[CH:29]=1>>[CH2:1]([O:8][C:9](=[O:24])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([O:35][CH3:36])[CH:29]=3)[N:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 16693-MethoxytyramineHCID 86603274[4-(2-Chloro-pyrimidin-4-yl)-phenyl]-carbamic acid benzyl ester

Product 1

HCID 58603766(4-{2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-carbamic acid benzyl ester

Procedure

Intermediate 48 was coupled with 4-(2-Amino-ethyl)-2-methoxy-phenol following procedure F. LC-MS showed the product had the expected M+H+ of 471. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.28 (m, 1H) 8.0 (d, 2H) 7.5 (d, 2H) 7.4 (m, 4H) 7.05 (s, 1H) 6.9 (d, 1H) 6.83 (m, 1H) 6.7 (m, 2H) 5.55 (br s, 1H) 5.21 (s, 2H) 3.81 (s, 3H) 3.7 (t, 2H) 2.9 (t, 2H).

Sources & evidence

ORD record
ord-282943bf8d7d4042bf9c075a053b8602
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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