Phenethylamine → 9-Bromo-5-phenethylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52480Notes

Reaction equation

HRID 52480 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](O)=[O:18])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH2:20]([NH2:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](=[O:18])[NH:28][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 99053359-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 538621449-Bromo-5-phenethylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 84%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (300 mg, 0.92 mmol) and phenethylamine (121 mg, 1.0 mmol) to give 330 mg of the title compound(84%): mp>250° C.; 1H NMR (270 MHz, DMSO-d6) δ12.12 (s, 1H), 8.21 (t, 1H, J=5.6 Hz), 7.09~7.39 (m, 7H), 5.07 (m, 1H), 3.24~3.33 (m, 2H), 2.64~2.73 (m, 3H), 2.25~2.32 (m, 2H), 1.80~1.95 (m, 1H).

Sources & evidence

ORD record
ord-e6a95aaa36074059b53612bf5d489ca3
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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