Phenethylamine → 8-Bromo-5-(2-phenylethylcarbamoyl)-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

HRID 52468Notes

Reaction equation

HRID 52468 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([C:16]([OH:18])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH2:27])=[CH:21][CH:20]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([C:16](=[O:18])[NH:27][CH2:26][CH2:25][C:22]3[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=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 99955808-Bromo-5-carboxy-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 199632308-Bromo-5-(2-phenylethylcarbamoyl)-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dioneYield 96.3%

Procedure

A procedure similar to that described in Example 5 was carried out with 8-bromo-5-carboxy-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione (300 mg, 0.96 mmol) and β-phenethylamine (133 μL, 1.061 mmol) to give 383 mg of the title compound (96%): mp 246°~249° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.01 (s, 1H), 8.41 (t, 1H, J=5.6 Hz), 7.25 (m, 5H), 7.22 (d, 1H, J=1 Hz), 7.07 (d, 1H, J=1 Hz), 5.07 (dd, 1H, J=10, 5 Hz), 3.65 (dd, 1H, J=17, 10 Hz), 3.30 (dt, 2H, J=5.6, 7 Hz), 3.04 (dd, 1H, J=17, 5 Hz), 2.71 (t, 2H, J=7 Hz).

Sources & evidence

ORD record
ord-af85d2bc7ffd471b9aacf4bbf20d0da4
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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