Diisopropylethylamine → 4-[(2-{[6-(2,4-Dichlorophenyl)-5-nitropyrazin-2-yl]amino}ethyl)amino]benzenecarbonitrile

HRID 396163Notes

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[N:28]=[CH:27][C:26]([C:29]#N)=[CH:25][CH:24]=1.[CH:31](N(C(C)C)CC)(C)C>CN(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]([NH:19][CH2:20][CH2:21][NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]#[N:28])=[CH:29][CH:31]=2)[CH:12]=[N:11][C:10]=1[N+:16]([O-:18])=[O:17]

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), 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile (10.0 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

concentrationThe crude mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-6d240c93861d4547a224d7c27ccdb32f
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608063B2

Reaction notes

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