5-Hydroxydopamine → HCID 58603460, compound

HRID 14724Notes

Reaction equation

HRID 14724 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=2)[CH:18]=1)[S:12]([CH3:15])(=[O:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].[NH2:31][CH2:32][CH2:33][C:34]1[CH:35]=[C:36]([OH:42])[C:37]([OH:41])=[C:38]([OH:40])[CH:39]=1>>[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:31][CH2:32][CH2:33][C:34]3[CH:35]=[C:36]([OH:42])[C:37]([OH:41])=[C:38]([OH:40])[CH:39]=3)[N:24]=2)[CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 1147725-HydroxydopamineHCID 86603242(3-{[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-methanesulfonyl-amino}-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 58603460HCID 58603460, compound

Procedure

Intermediate 4 was coupled with 5-(2-Amino-ethyl)-benzene-1,2,3-triol following procedure F. LC-MS showed the product had the expected M+H+ of 588. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.2 (m, 2H) 8.0 (m, 1H) 7.6 (m, 2H) 7.3 (m, 3H) 4.8 (m, 1H) 4.5 (s, 2H) 3.9 (m, 2H) 3.3 (m, 2H) 3.0 (m, 2H) 2.9 (m, 5H) 1.6 (m, 2H) 1.4 (s, 9H).

Sources & evidence

ORD record
ord-7d432f39762a449687b6a727495957ec
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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