Water → [3-Cyano-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2-pyrazinyl]formamide

HRID 915030Notes

Reaction equation

[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:12]=[C:13]([C:25]#[N:26])[C:14](C#N)=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:5]1)([CH3:3])[CH3:2].[CH:27]([N-:29]C=O)=[O:28].[Na+].O>CC(N(C)C)=O>[C:25]([C:13]1[C:14]([NH:29][CH:27]=[O:28])=[N:15][C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=2)[N:12]=1)#[N:26]

Participants

Conditions

Temperature: 102.5 °C

Procedure

A suspension of 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2,3-pyrazinedicarbonitrile (343 mg) and sodium diformylamide (190 mg) in DMA (1 ml) was heated at 100-105° C. for an hour. After addition of water, the reaction mixture was extracted with CHCl3, dried over MgSO4, concentrated under reduced pressure and subjected to column chromatography on silica gel. With elution of a mixture of n-hexane and EtOAc (50:50 v/v) was obtained [3-cyano-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2-pyrazinyl]formamide as a solid (30 mg) and with elution of a mixture of n-hexane and EtOAc (30:70 v/v) was obtained [3-cyano-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinyl]-formamide as a solid (22 mg).

Workup

extractionthe reaction mixture was extracted with CHCl3
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
washWith elution of a mixture of n-hexane

Sources & evidence

ORD record: ord-d5d887bbc01944a2bb97fc4339eb5ac3
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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