Dimethyl Sulfoxide → HCID 69333289, compound

HRID 915084Notes

Reaction equation

HRID 915084 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]([C:11]1[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH:18]([CH3:20])[CH3:19])[N:12]=1)=O.[NH2:22]/[C:23](=[C:26](\[NH2:29])/[C:27]#[N:28])/[C:24]#[N:25].CS(C)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:22]=[C:23]([C:24]#[N:25])[C:26]([C:27]#[N:28])=[N:29][C:9]=1[C:11]1[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH:18]([CH3:20])[CH3:19])[N:12]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 2723951DiaminomaleonitrileHCID 69331926HCID 69331926, compound

Product 1

HCID 69333289HCID 69333289, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(2-bromophenyl)-2-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-1,2-ethanedione (5.30 g) and (2Z)-2,3-diamino-2-butenedinitrile (1.65 g) in a solution of DMSO (0.25 ml) and toluene (25 ml) was refluxed for 8 hours. The mixture was concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (85:15 v/v) to give 5-(2-bromophenyl)-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2,3-pyrazinedicarbonitrile as a solid (3.58 g).

Workup

  1. temperaturewas refluxed for 8 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a residue
  4. customThe residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (85:15 v/v)

Sources & evidence

ORD record
ord-95ca57b4cfec485baafbec8db6d6b8fc
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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