Aniline → 9-Chloro-5-phenylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52559Notes

Reaction equation

HRID 52559 reaction equation
[Cl: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.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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 103571279-chloro-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 100220259-Chloro-5-phenylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 60%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-chloro-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (200 mg, 0.68 mmol) and aniline (200 mg, 2.15 mmol) to give 150 mg of the title compound (60%):mp >280° C.; 1H NMR (270 MHz, DMSO-d6) δ12.09 (bs, 1H), 10.02 (s, 1H), 7.57 (d, 2H, J=7.8 Hz), 7.30 (t, 2H, J=7.8 Hz), 7.14 (s, 1H), 7.06 (t, 1H, J=7.8 Hz), 7.05 (s, 1H), 5.14~5.29 (m, 1H), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.82 (dm, 1H, J=17.1 Hz), 2.55~2.70 (m, 2H), 2.10 (dm, 1H, J=13.5 Hz), 1.80~1.96 (m, 1H).

Sources & evidence

ORD record
ord-bc5cc9638ae2418f8627ba24dc7a855f
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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