Tyramine → HCID 58603724, compound

HRID 14877Notes

Reaction equation

HRID 14877 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=3)[CH:20]=2)[CH2:16][CH3:17])[CH2:9]1)=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>>[CH2:16]([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:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)[N:26]=2)[CH:22]=[CH:23][CH:24]=1)[CH2:14][C@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1)[CH3:17]

Participants

3

Reactant 2

HCID 5610TyramineHCID 866032973-({[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-ethyl-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603724HCID 58603724, compound

Procedure

Intermediate 95 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 8.66 (s, 1H), 8.38 (d, 1H), 8.35 (s, 1H), 7.94 (d, 1H), 7.75 (t, 1H), 7.67 (d, 1H), 7.11 (d, 2H), 6.68 (d, 2H), 4.57 (s, 2H), 3.94 (s, 2H), 3.13 (m, 2H), 2.82 (m, 6H), 2.65 (t, 1H), 2.34 (m, 2H), 1.74 (m, 4H), 1.24 (t, 3H).

Sources & evidence

ORD record
ord-38c4c5cc19264c1985074757a56603a9
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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