Benzylamine → 9-Bromo-5-benzylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52479Notes

Reaction equation

HRID 52479 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](O)=[O:18])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](=[O:18])[NH:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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 7504BenzylamineHCID 99053359-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 544661719-Bromo-5-benzylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 81.3%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (300 mg, 0.92 mmol) and benzylamine (107 mg, 1.0 mmol) to give 310 mg of the title compound (81%): mp>250° C.; 1H NMR (270 MHz, DMSO-d6) δ12.12 (s, 1H), 8.68 (t, 1H, J=6.1 Hz), 7.12~7.31 (m, 7H), 5.13~5.19 (m, 1H), 4.26 (d, 2H, J=6.1 Hz), 2.78 (dm, 1H, J=16.8 Hz), 2.39~2.61 (m, 2H), 1.85~2.00 (m, 1H).

Sources & evidence

ORD record
ord-5bb509011ff44baaad2b90c90e873b75
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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