m-Tyramine → 3-{2-[4-(3-{[Ethyl-(2(S)-pyrrolidin-2-yl-ethyl)-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

HRID 14889Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH2:14][N:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=2)[CH:20]=1)[CH2:16][CH3:17])=O)(C)(C)C.[NH2:32][CH2:33][CH2:34][C:35]1[CH:36]=[C:37]([OH:41])[CH:38]=[CH:39][CH:40]=1>>[CH2:16]([N:15]([CH2:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:32][CH2:33][CH2:34][C:35]3[CH:36]=[C:37]([OH:41])[CH:38]=[CH:39][CH:40]=3)[N:26]=2)[CH:22]=[CH:23][CH:24]=1)[CH2:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[CH3:17]

Participants

Reactant 2

HCID 11492m-Tyramine

HCID 866033002-(2-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586034653-{2-[4-(3-{[Ethyl-(2(S)-pyrrolidin-2-yl-ethyl)-amino]-methyl}-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Procedure

Intermediate 107 was coupled with 3-(2-Amino-ethyl)-phenol following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 447. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.62 (s, 1H), 8.36 (d, 2H), 7.94 (d, 1H), 7.72 (t, 1H), 7.66 (d, 1H), 7.05 (t, 1H), 6.78 (s, 2H), 6.59 (d, 1H), 4.53 (m, 2H), 3.90 (m, 2H), 3.58 (m, 2H), 3.32 (m, 5H), 3.00 (t, 2H), 2.22 (m, 3H), 2.02 (m, 2H), 1.71 (m, 1H), 1.40 (t, 3H).

Sources & evidence

ORD record: ord-5f4797c29ec14cb392d614101ed312dd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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