3'-Aminoacetophenone → 9-Bromo-5-(m-acetylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52512

Reaction equation

HRID 52512 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([OH:20])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[C:21]([C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27])(=[O:23])[CH3:22]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:20])[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[C:24]([C:21](=[O:23])[CH3:22])[CH:25]=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 74173'-AminoacetophenoneHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 537396089-Bromo-5-(m-acetylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 87.7%

Procedure

A procedure similar to that described in Example 51 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (170 mg, 0.5 mmol) and m-acetylaniline (80 mg, 0.59 mmol) to give 200 mg of the title compound (85%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (bs, 1H), 10.23 (s, 1H), 8.12 (bs, 1H), 7.85 (d, 1H, J=8.1 Hz), 7.68 (d, 1H, J=8.1 Hz), 7.47 (t, 1H, J=8.1 Hz), 7.24 (d, 1H, J=2 Hz), 7.17 (d, 1H, J=2 Hz), 5.18~5.28 (m, 1H), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.55~2.70 (m, 2H), 2.56 (s, 3H), 2.12 (dm, 1H, J=13.5 Hz), 1.81~1.96 (m, 1H).

Sources & evidence

ORD record
ord-24a184e70b4d4c87a75f04b12a965ebb
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Linked notes

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