Ethyl 3-aminobenzoate → 9-Bromo-5-(m-ethoxycarbonylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52501

Reaction equation

HRID 52501 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH2:21]([O:23][C:24]([C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29])=[O:25])[CH3:22]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[C:26]([C:24]([O:23][CH2:21][CH3:22])=[O:25])[CH:27]=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 11400Ethyl 3-aminobenzoateHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 544131859-Bromo-5-(m-ethoxycarbonylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 89%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (400 mg, 1.18 mmol) and m-ethoxycarbonylaniline (250 μL, 1.5 mmol) to give 510 mg of the title compound (89%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (bs, 1H), 10.25 (s, 1H), 8.20 (bs, 1H), 7.85 (d, 1H, J=8.1 Hz), 7.65 (d, 1H, J=8.1 Hz), 7.30 (t, 1H, J=8.1 Hz), 7.24 (d, 1H, J=2Hz), 7.17 (d, 1H, J=2 Hz), 5.16~5.27 (m, 1H), 4.32 (q, 2H, J=7.2 Hz), 3.05 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.55~2.68 (m, 2H), 2.12 (dm, 1H, J=13.5 Hz), 1.81~1.97 (m, 1H), 1.33 (t, 3H, J=7.1 Hz).

Sources & evidence

ORD record
ord-696dce6d1bac4d5cb16b1a5ffb094259
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Linked notes

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