Tyramine → HCID 58603523, compound

HRID 2386497Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[CH2:10][CH:9]1[CH2:28][CH:29]([CH3:31])[CH3:30])=O)(C)(C)C.[NH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1>>[CH2:28]([C@@H:9]1[NH:8][CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:32][CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=4)[N:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:10]1)[CH:29]([CH3:30])[CH3:31]

Participants

Reactant 2

HCID 5610Tyramine

HCID 866033074-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2-isobutyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603523HCID 58603523, compound

Procedure

Intermediate 113 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 447. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.65 (s, 1H), 8.36 (d, 1H), 8.32 (s, 1H), 7.95 (d, 1H), 7.71 (t, 1H), 7.65 (d, 1H), 7.11 (d, 1H), 6.68 (s, 1H), 4.70 (d, 1H), 4.57 (d, 1H), 3.96 (m, 2H), 3.81 (m, 2H), 3.58 (m, 4H), 3.40 (t, 1H), 2.92 (t, 2H), 1.75 (m, 1H), 1.62 (t, 2H), 1.00 (d, 3H), 0.98 (d, 3H).

Sources & evidence

ORD record: ord-4d90f0b817fa4c8daf6d83e9ad055c1b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268822B2

Reaction notes

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