Water → HCID 69331848, compound

HRID 915065Notes

Reaction equation

HRID 915065 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[N:6][C:7]=1Br.C(N)C1C=CC=CC=1.O.C[C:35]([N:37](C)[CH3:38])=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[N:6][C:7]=1[N:37]([CH3:38])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 31374DimethylacetamideHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 69331848HCID 69331848, 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-isopropyl-3(2H)-pyridazinone (100 mg) and benzylamine (0.085 ml) in DMA (0.2 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 preparative TLC on silica gel (CHCl3 only). A less polar zone was gave 6-[5-amino-6-(dimethylamino)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone as a solid (18 mg) and a more polar zone was gave 6-[5-amino-6-(benzylamino)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone as a solid (67 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 preparative TLC on silica gel (CHCl3 only)

Sources & evidence

ORD record
ord-fe490790d62b4f7ab12500e19fefe539
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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