Tyramine → 4-(2-{4-[3-(Isopropylamino-methyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

HRID 14841Notes

Reaction equation

HRID 14841 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])[CH:5]=[CH:4][N:3]=1.[NH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>>[CH:13]([NH:12][CH2:11][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:7]=2)[CH:18]=[CH:17][CH:16]=1)([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 5610TyramineHCID 86603283[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-isopropyl-amine

Product 1

HCID 670449214-(2-{4-[3-(Isopropylamino-methyl)-phenyl]-pyrimidin-2-ylamino}-ethyl)-phenol

Procedure

Intermediate 65 was coupled with tyramine following procedure F. The product was purified by HPLC. LC-MS showed the product had the expected M+H+ of 363. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.3 (m, 1H), 8.2 (m, 2H), 8.1 (m, 2H), 7.5 (d, 2H), 7.2 (m, 2H), 7.1 (d, 1H), 7.0 (d, 2H), 6.7 (d, 2H), 3.8 (m, 1H), 3.3 (m, 4H), 2.7 (m, 1H), 1.1 (m, 6H).

Workup

  1. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-e6859b262bc944bd9b23c80b0615f570
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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