Aniline → 8-Bromo-5-phenylcarbamoylmethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

HRID 52475Notes

Reaction equation

HRID 52475 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH2:16][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.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH2:16][C:17](=[O:18])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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 6115AnilineHCID 100191838-bromo-5-carboxymethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 99783038-Bromo-5-phenylcarbamoylmethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dioneYield 51.2%

Procedure

A procedure similar to that described in Example 5 was carried out with 8-bromo-5-carboxymethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione (130 mg, 0.40 mmol) and aniline (40 μL, 0.44 mmol) to give 82 mg of the title compound (51%): mp 186° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.23 (s, 1H), 10.34 (s, 1H), 7.55 (d, 2H, J=8 Hz), 7.32 (t, 2H, J=8 Hz), 7.22 (s, 2H), 7.07 (t, 1H, J=8 Hz), 5.30~5.36 (m, 1H), 2.86 (dm, 1H, J=18 Hz), 2.75 (dm, 1H, J=14 Hz), 2.62 (m, 1H, J=14 Hz), 2.02~2.18 (m, 1H).

Sources & evidence

ORD record
ord-a56a6729d90f4db7844f25442ddaaf48
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

Loading…