Water → 6-(5-amino-6-chloro-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

HRID 915034Notes

Reaction equation

HRID 915034 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:17])[N:12]([CH:14]([CH3:16])[CH3:15])[N:13]=2)=[N:6][CH:7]=1.[Cl:24]N1C(=O)CCC1=O.O.CCOC(C)=O>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:17])[N:12]([CH:14]([CH3:16])[CH3:15])[N:13]=2)=[N:6][C:7]=1[Cl:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 115657766-(5-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone

Product 1

HCID 866009136-(5-amino-6-chloro-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinoneYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(5-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (50 mg), N-chlorosuccinimide (23.9 mg) in DMF (1.5 ml) was stirred at 60° C. for 2 hours. Water and EtOAc were added to the reaction mixture. The organic layer was separated, and dried over Na2SO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of CHCl3 and MeOH. The fractions were concentrated in vacuo to obtain 6-(5-amino-6-chloro-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (30 mg) as white powder.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluted with a mixture of CHCl3 and MeOH
  6. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-14026b52e5994a73820bcd44a0881337
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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