Water → HCID 69332654, compound

HRID 915066Notes

Reaction equation

HRID 915066 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]([NH2:29])[CH2:26][CH2:27][CH3:28].O>CN1CCN(C)C1=O.CC(C)=O>[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[NH:29][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 8007ButylamineHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 69332654HCID 69332654, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
122.5 °C

Procedure

In a sealed tube, a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg) and butylamine (0.116 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), a precipitate was collected by filtration and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v) to give a solid. The solid was suspended in acetone to give 6-[5-amino-6-(butylamino)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (71 mg).

Workup

  1. filtrationa precipitate was collected by filtration
  2. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v)
  3. customto give a solid

Sources & evidence

ORD record
ord-eb06ef9feaf84000960c74a0adc48ef5
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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