Aniline → HCID 54313479, compound

HRID 52548Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH:17]([C:19](O)=[O:20])[CH3:18])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH:17]([C:19](=[O:20])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:18])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

Reactant 2

HCID 6115Aniline

HCID 54551255HCID 54551255, compound

Product 1

HCID 54313479HCID 54313479, compoundYield 41%

Procedure

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-(1-carboxyethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (more polar) (100 mg, 0.28 mmol) and aniline (28 μL, 0.31 mmol) to give 50 mg of the title compound (41%): mp>300° C.; 1H NMR (270 MHz, DMSO-d6) δ11.92 (s, 1H), 9.46 (s, 1H), 7.32 (d, 2H, J=8 Hz), 7.23 (t, 1H, J=8 Hz), 7.21 (s, 1H), 7.19 (s, 1H), 6.99 (t, 1H, J=8 Hz), 5.13 (bd, 1H, J=9 Hz), 2.73~2.99 (m, 2H), 2.59 (qd, 1H, J=9, 7 Hz), 2.28 (dm, 1H, J=13.5 Hz), 1.72~1.92 (m, 1H), 1.13 (d, 3H, J=7 Hz).

Sources & evidence

ORD record: ord-e593f978c0ca4a5e8a2733060156e69f
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616586

Reaction notes

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