2-Methoxyaniline → 9-Bromo-5-(o-methoxyphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52508Notes

Reaction equation

HRID 52508 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.[CH3:21][O:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[O:22][CH3:21])[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 70002-MethoxyanilineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 540675119-Bromo-5-(o-methoxyphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 86.6%

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 (150 mg, 0.442 mmol) and o-methoxyaniline (76 mg, 0.62 mmol) to give 170 mg of the title compound (86%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.06 (bs, 1H), 9.27 (s, 1H), 7.88 (d, 1H, J=8.1 Hz), 7.24 (s, 1H), 7.17 (s, 1H), 7.08 (t, 1H, J=8.1 Hz), 7.03 (d, 1H, J=8.1 Hz), 6.90 (t, 1H, J=8.1 Hz), 5.16~5.27 (m, 1H), 3.81 (s, 3H), 3.12 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.81 (dm, 1H, J =17.1 Hz), 2.77 (dd, 1H, J=13.5, 10.8 Hz), 2.62 (dd, 1H, J=13.5, 5.4 Hz), 2.11 (dm, 1H, J=13.5 Hz), 1.77~1.95 (m, 1H).

Sources & evidence

ORD record
ord-1c8645478e0549ce93213703eee04b83
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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