4-Chlorobenzylamine → N-(4-Chlorobenzyl)-9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]-quinoxaline-6-carboxamide

HRID 1168518Notes

Reaction equation

HRID 1168518 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:16](=[O:17])[C:15]([C:18]([O:20]CC)=O)=[CH:14][N:6]3[CH2:7][C:8](=[O:13])[N:9]([CH3:12])[C:10]([CH:11]=1)=[C:5]23.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>C(#N)C>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:18]([C:15]2[C:16](=[O:17])[C:4]3[C:5]4[N:6]([CH:14]=2)[CH2:7][C:8](=[O:13])[N:9]([CH3:12])[C:10]=4[CH:11]=[C:2]([I:1])[CH:3]=3)=[O:20])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 12083043Ethyl 9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxylate

Product 1

HCID 12083044N-(4-Chlorobenzyl)-9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]-quinoxaline-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 9-iodo-1-methyl-2,7-dioxo-2,3-dihydro-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxylate (Preparation 22, 400 mg) is stirred at 180° C. in 4-chlorobenzylamine (2.0 mL) for 1 h. The mixture is cooled and diluted with acetonitrile to give 412 mg of the title compound. Physical characteristics: M.p. 278-283° C.; 1H NMR (DMSO-d6) δ3.38, 4.55, 5.21, 7.35, 7.39, 7.69, 8.18, 8.76, 10.12. Anal. Found: C, 47.43; H, 3.01; N, 8.32; Cl, 7.14.

Workup

  1. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-4ef9c461c9e6433dbc8a99d9d0e2977b
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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