Aniline → HCID 44285323, compound

HRID 52519Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C@H:16]([CH3:17])[CH2:15][C@@H:14]([CH2:18][C:19](O)=[O:20])[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[C@H:16]([CH3:17])[CH2:15][C@@H:14]([CH2:18][C:19](=[O:20])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[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 44285413HCID 44285413, compound

Product 1

HCID 44285323HCID 44285323, compoundYield 88%

Procedure

A procedure similar to that described in Example 5 was carried out with trans-9-bromo-5-carboxymethyl-7-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (90 mg, 0.255 mmol) and aniline (25 μL, 0.28 mmol) to give 96 mg of the title compound (88%): mp>300° C.; 1H NMR (270 MHz, DMSO-d6) δ12.09 (bs, 1H), 7.56 (d, 2H, J=7.3 Hz), 7.32 (d, 1H, J=2 Hz), 7.30 (t, 2H, J=7.3 Hz), 7.21 (d, 1H, J=2 Hz), 7.05 (t, 1H, J=7.3 Hz), 5.15~5.25 (m, 1H), 3.19 (ddq, 1H, J=12.5, 4.6, 6.6 Hz), 2.55~2.70 (m, 2H), 2.13 (ddd, 1H, J=14.2, 4.6, 2.3 Hz), 1.67 (ddd, 1H, J=14.2, 12.5, 4.9 Hz), 1.33 (d, 3H, J=6.3 Hz).

Sources & evidence

ORD record: ord-a0572b808a2e4f70b0f988cd2fb223b4
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616586

Reaction notes

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