Aniline → HCID 54313479, compound

HRID 52547Notes

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 58%

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 (less polar) (100 mg, 0.28 mmol) and aniline (28 μL, 0.31 mmol) to give 70 mg of the title compound (58%): mp>300° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (s, 1H), 10.00 (s, 1H), 7.52 (d, 2H, J=8 Hz), 7.29 (t, 1H, J=8 Hz), 7.19 (s, 1H), 7.17 (s, 1H), 7.05 (t, 1H, J=8 Hz), 5.19 (bd, 1H, J=9 Hz), 3.10 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.67~2.84 (m, 2H, J=17.1 Hz), 2.01 (dm, 1H, J=13.5 Hz), 1.72~1.92 (m, 1H), 1.02 (d, 3H, J=7 Hz).

Sources & evidence

ORD record: ord-d9bd2728964e4cb3a71e9db923ad0355
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616586

Reaction notes

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