2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-Amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile

HRID 915023Notes

Reaction equation

[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]([NH:19]CC3C=CC(OC)=CC=3)=[N:13][C:12]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:5]1)([CH3:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.CCCCCC.CCOC(C)=O>O.C(Cl)(Cl)Cl>[NH2:19][C:14]1[C:15]([C:17]#[N:18])=[N:16][C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)=[C:12]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:13]=1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a solution of 6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-5-phenyl-2-pyrazinecarbonitrile (590 mg) in a mixture of water (1.5 ml) and CHCl3 (30 ml) was added 4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile (888 mg). The reaction mixture was stirred at 25-30° C. for 10 hours, washed with 1N aq. NaOH solution, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile as a solid (335 mg).

Workup

washwashed with 1N aq. NaOH solution
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customto give a residue

Sources & evidence

ORD record: ord-132f337563bf499f9fa192c131c295c9
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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