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

HRID 52491Notes

Reaction equation

HRID 52491 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH:20]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([C:17](=[O:19])[NH:26][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]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 7965CyclohexylamineHCID 99053359-bromo-5-carboxy-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 542906299-Bromo-5-cyclohexylcarbamoyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 91%

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 cyclohexylamine (100 mg, 1.0 mmol) to give 340 mg of the title compound (91%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.14 (s, 1H), 8.03 (d, 1H, J=7.9 Hz), 7.16 (bs, 1H), 7.14 (bs, 1H), 5.08~5.13 (m, 1H), 3.42~3.59 (m, 1H), 2.79 (dm, 1H, J=16.8 Hz), 2.45~2.63 (m, 1H), 2.36 (dm, 1H, J=13.5 Hz), 1.85~2.02 (m, 1H), 1.63~1.74 (m, 4H), 1.05~1.33 (m, 6H).

Sources & evidence

ORD record
ord-fae221701ecd42939a6f5ceea62eb152
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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