Water → HCID 69331839, compound

HRID 915070Notes

Reaction equation

HRID 915070 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[N:14]=2)=[N:6][C:7]=1Br.C(N)C1C=CC=CC=1.O.C[C:33]([N:35](C)[CH3:36])=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[N:14]=2)=[N:6][C:7]=1[N:35]([CH3:36])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 31374DimethylacetamideHCID 86074880HCID 86074880, compound

Product 1

HCID 69331839HCID 69331839, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
122.5 °C

Procedure

A mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-methyl-3(2H)-pyridazinone (150 mg) and benzylamine (0.138 ml) in DMA (0.3 ml) was heated at 120-125° C. for 50 hours. After addition of water (4 ml), an aqueous layer was removed by decantation to give a residue. The residue was dissolved in CHCl3, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel. By elution with a mixture of n-hexane and EtOAc (60:40 v/v) was obtained 6-[5-amino-6-(dimethylamino)-3-phenyl-2-pyrazinyl]-2-methyl-3(2H)-pyridazinone as a solid (83 mg) and by elution with a mixture of n-hexane and EtOAc (20:80 v/v) was obtained 6-[5-amino-6-(benzylamino)-3-phenyl-2-pyrazinyl]-2-methyl-3(2H)-pyridazinone as a solid (48 mg).

Workup

  1. customan aqueous layer was removed by decantation
  2. customto give a residue
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography on silica gel
  6. washBy elution
  7. additionwith a mixture of n-hexane

Sources & evidence

ORD record
ord-7512583007b742078652bad149eadf2f
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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