Tyramine → HCID 58603750, compound

HRID 14881Notes

Reaction equation

HRID 14881 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:17]=2)[CH2:13][CH3:14])[CH2:9]1)=O)(C)(C)C.[NH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1>>[NH:8]1[CH2:9][CH:10]([N:12]([CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:29][CH2:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=4)[N:23]=3)[CH:19]=[CH:20][CH:21]=2)[CH2:13][CH3:14])[CH2:11]1

Participants

3

Reactant 2

HCID 5610TyramineHCID 866032993-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603750HCID 58603750, compound

Procedure

Intermediate 105 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 405. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.69 (s, 1H), 8.40 (d, 1H), 8.34 (s, 1H), 7.96 (d, 1H), 7.72 (t, 1H), 7.68 (d, 1H), 7.11 (d, 2H), 6.67 (d, 2H), 4.56 (m, 5H), 3.78 (m, 4H), 3.21 (q, 2H), 2.93 (t, 2H), 1.39 (t, 3H).

Sources & evidence

ORD record
ord-f334f97e557a44a3a7372e7fb84e240f
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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