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

HRID 52504

Reaction equation

HRID 52504 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH:21]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:27][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]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 7965CyclohexylamineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 442857059-Bromo-5-cyclohexylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 86.1%

Procedure

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (150 mg, 0.442 mmol) and cyclohexylamine (50 mg, 0.51 mmol) to give 160 mg of the title compound (86%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.04 bs, 1H), 7.86 (d, 1H, J=7.6 Hz), 7.21 (s, 1H), 7.15 (s, 1H), 5.03~5.18 (m, 1H), 3.43~3.60 (m, 1H), 3.03 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.76 (dm, 1H, J=17.1 Hz), 2.36 (dd, 1H, J=16.2, 4.5 Hz), 2.28 (dd, 1H, J=16.2, 11.7 Hz), 1.98 (dm, 1H, J=13.5 Hz), 1.50~1.86 (m, 5H), 1.03~1.36 (m, 6H).

Sources & evidence

ORD record
ord-e29f4541219c4120840d88d94ac23264
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Linked notes

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