N,N-Dimethylethylenediamine → HCID 69331921, compound

HRID 915068Notes

Reaction equation

HRID 915068 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.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][NH2:29]>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][CH2:28][CH2:27][N:26]([CH3:30])[CH3:25]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 866009156-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 69331921HCID 69331921, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 N,N-dimethyl-1,2-ethanediamine (0.127 ml) in 1,2-dimethyl-2-imidazolidinone (0.3 ml) was heated at 120-125° C. for 50 hours. After addition of water (3 ml), the mixture was extracted with CHCl3, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel [Chromatorex® NH] eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give a syrup. The syrup was crystallized from a mixture of acetone and n-hexane to give 6-(5-amino-6-{[2-(dimethylamino)ethyl]amino}-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (36 mg).

Workup

  1. extractionthe mixture was extracted with CHCl3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography on silica gel [Chromatorex® NH]
  5. washeluting with a mixture of n-hexane and EtOAc (60:40 v/v)
  6. customto give a syrup
  7. customThe syrup was crystallized from a mixture of acetone and n-hexane

Sources & evidence

ORD record
ord-3c300be1c6f04aee84e8ac03deba469a
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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