Tyramine → HCID 58603663, compound

HRID 2386439Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=2)[CH2:11][NH:12][CH2:13][CH2:14][CH2:15][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH:5]=[CH:4][N:3]=1.[NH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1>>[CH2:17]([N:16]([CH2:19][CH3:20])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[N:7]=2)[CH:23]=[CH:22][CH:21]=1)[CH3:18]

Participants

Reactant 2

HCID 5610Tyramine

HCID 86652164HCID 86652164, compound

Product 1

HCID 58603663HCID 58603663, compound

Procedure

Intermediate 64 was coupled with tyramine following procedure F. LC-MS showed the product had the expected M+H+ of 434. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.4 (d, 1H), 8.2 (m, 2H), 8.1 (m, 1H), 8.0 (m, 1H), 7.5 (m, 3H), 7.2 (m, 1H), 7.1 (m, 4H), 6.6 (m, 2H), 4.2 (m, 1H), 3.5 (m, 2H), 2.7 (m, 3H), 2.6 (m, 6H), 1.7 (m, 2H), 1.0 (m, 6H).

Sources & evidence

ORD record: ord-53e48a0c36164cb9a3dd830351ed79f8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268822B2

Reaction notes

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