Tyramine → 4-{2-[4-(3-{[(3-Amino-propyl)-ethyl-amino]-methyl}-phenyl)-5-fluoro-pyrimidin-2-ylamino]-ethyl}-phenol

HRID 14856Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:26]([F:27])=[CH:25][N:24]=[C:23](Cl)[N:22]=2)[CH:16]=1)[CH2:12][CH3:13])(C)(C)C.[NH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1>>[NH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[C:26]([F:27])=[CH:25][N:24]=[C:23]([NH:30][CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)[N:22]=2)[CH:18]=[CH:19][CH:20]=1)[CH2:12][CH3:13]

Participants

Reactant 2

HCID 5610Tyramine

HCID 86603289(3-{[3-(2-Chloro-5-fluoro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 586036954-{2-[4-(3-{[(3-Amino-propyl)-ethyl-amino]-methyl}-phenyl)-5-fluoro-pyrimidin-2-ylamino]-ethyl}-phenol

Procedure

Intermediate 78 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 424. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.29 (d, 1H), 8.19 (s, 2H), 7.66 (m, 2H), 7.05 (d, 2H), 6.68 (d, 2H), 4.49 (s, 2H), 3.58 (t, 2H), 3.24 (m, 4H), 2.98 (t, 2H), 2.80 (t, 2H), 2.07 (m, 2H), 1.36 (t, 3H).

Sources & evidence

ORD record: ord-75f86b4174d04c2b871149f367bf0598
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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