Water → HCID 69332593, compound

HRID 915067Notes

Reaction equation

HRID 915067 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.[CH2:25]([NH2:28])[CH:26]=[CH2:27].O>CN1CCN(C)C1=O.C(Cl)(Cl)Cl>[CH2:25]([NH:28][C:7]1[N:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:3][C:2]=1[NH2:1])[CH:26]=[CH2:27]

Participants

6

Reactant 3

HCID 962WaterHCID 7853AllylamineHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 69332593HCID 69332593, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
122.5 °C

Procedure

A mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg) and allylamine (0.0881 ml) in 1,3-dimethyl-2-imidazolidinone (0.3 ml) was heated at 120-125° C. for 50 hours. After addition of water (3 ml), an aqueous layer was removed by decantation to give a residue. The residue was dissolved in CHCl3, dried over MgSO4 and concentrated under reduced pressure to give syrup. The syrup was crystallized from a mixture of acetone and hexane to give 6-[6-(allylamino)-5-amino-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (71 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. customto give syrup
  6. customThe syrup was crystallized from a mixture of acetone and hexane

Sources & evidence

ORD record
ord-fc6bd85f3b1d4d61a9bac110e8fd27e8
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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