Dimethylformamide → [6-(2,4-Dichlorophenyl)-5-nitropyrazin-2-yl]methyl{2-[(4-nitrophenyl)amino]ethyl}amine

HRID 396164Notes

Reaction equation

HRID 396164 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13](Br)[N:14]=1.NCCN(C)C1C=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25]N=1.C([N:36]([CH:39]([CH3:41])[CH3:40])[CH2:37][CH3:38])(C)C.[CH3:42][N:43](C=O)C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:43]([CH3:42])[CH2:38][CH2:37][NH:36][C:39]2[CH:40]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:41]=2)[CH:12]=[N:11][C:10]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 223185103-(2,4-Dichlorophenyl)-5-bromo-2-nitropyrazineHCID 22318515(2-Aminoethyl)methyl(5-nitro(2-pyridyl))amine

Product 1

HCID 86583876[6-(2,4-Dichlorophenyl)-5-nitropyrazin-2-yl]methyl{2-[(4-nitrophenyl)amino]ethyl}amine

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(2,4-dichlorophenyl)-5-bromo-2-nitropyrazine (20 mg, 0.057 mmol) in DMF (1 ml), (2-aminoethyl)methyl(5-nitro(2-pyridyl))amine (12.0 mg, 0.06 mmol) and diisopropylethyl amine (40 μl, 0.228 mmol) were added. The reaction mixture was stirred for 12 hours at 80° C. The crude mixture was concentrated in vacuo and subjected to column chromatography (5% methanol in methylene chloride) to afford the title compound as bright yellow solid.

Workup

  1. concentrationThe crude mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-09bf10ed7cd74b75934ce1a845e0835c
Source dataset
uspto-grants-2003_08
Patent number
US06608063B2

Reaction notes

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