Diisopropylethylamine → {2-[(3-Amino-4-nitrophenyl)amino]ethyl}[6-(2,4-dichlorophenyl)-5-nitropyrazin-2-yl]amine

HRID 396161Notes

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.[NH2:19][CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([NH2:32])N=1.[CH:33](N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:32][C:25]1[CH:33]=[C:23]([NH:22][CH2:21][CH2:20][NH:19][C:13]2[CH:12]=[N:11][C:10]([N+:16]([O-:18])=[O:17])=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:14]=2)[CH:28]=[CH:27][C:26]=1[N+:29]([O-:31])=[O:30]

Participants

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)(6-amino-5-nitro(2-pyridyl))amine (12.3 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

concentrationThe crude mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-9b4616afcbbd4d09b689d4c6ad595161
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608063B2

Reaction notes

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