Water → HCID 86600907, compound

HRID 915015Notes

Reaction equation

HRID 915015 reaction equation
[NH2:1][C:2]1[C:3]([C:19]#[N:20])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[N:10]=2)=[CH:6][N+:7]=1[O-].P(Cl)(Cl)([Cl:23])=O.O.[CH3:27][N:28]([CH:30]=O)[CH3:29]>>[Cl:23][C:6]1[N:7]=[C:2]([N:1]=[CH:27][N:28]([CH3:30])[CH3:29])[C:3]([C:19]#[N:20])=[N:4][C:5]=1[C:9]1[CH:14]=[CH:13][C:12](=[O:15])[N:11]([CH:16]([CH3:18])[CH3:17])[N:10]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178456629HCID 178456629, compound

Product 1

HCID 86600907HCID 86600907, compound

Procedure

A solution of 3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinecarbonitrile 4-oxide (1.54 g) in DMF (30 ml) was stirred at 0° C. Phosphorous oxychloride (1.58 ml) was dropped to the solution and the reaction mixture was stirred under same condition for 3 hours. Water was added to the reaction mixture. The reaction mixture was stirred at 20° C. for 20 hours to give a yellow precipitate. The precipitate was collected by filtration to obtain yellow powder. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain N′-[6-chloro-3-cyano-5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-pyrazinyl]-N,N-dimethylimidoformamide (1.0 g) as white powder.

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for 20 hours
  2. customto give a yellow precipitate
  3. filtrationThe precipitate was collected by filtration
  4. customto obtain yellow powder
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with a mixture of n-hexane and EtOAc
  7. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-85f682d5fa834a0192251a255683e0ab
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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