Hydrochloric Acid → HCID 69331825, compound

HRID 915078Notes

Reaction equation

HRID 915078 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:12][C:13]1[N:14]=[C:15]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:16]([C:23]2[CH:24]=[CH:25][C:26](=[O:32])[N:27]([CH:29]([CH3:31])[CH3:30])[N:28]=2)=[N:17][C:18]=1S(C)(=O)=O.Cl>C(Cl)(Cl)Cl>[NH2:12][C:13]1[N:14]=[C:15]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:16]([C:23]2[CH:24]=[CH:25][C:26](=[O:32])[N:27]([CH:29]([CH3:31])[CH3:30])[N:28]=2)=[N:17][C:18]=1[O:11][CH2:10][CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 60542-PhenylethanolHCID 24758Sodium hydrideHCID 69331470HCID 69331470, compound

Product 1

HCID 69331825HCID 69331825, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
27.5 °C

Procedure

To a suspension of NaH (60% in oil suspension) (31.1 mg) in 1,2-dimethyl-2-imidazolidinone (0.6 ml) was added 2-phenylethanol (0.094 ml) and the mixture was stirred at 25-30° C. for 30 minutes. 6-[5-Amino-6-(methylsulfonyl)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (150 mg) was added and the mixture was heated at 100-105° C. for 15 hours. To the mixture was added 0.1N HCl (3 ml) and 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 column chromatography on silica gel. By elution with a mixture of n-hexane and EtOAc (60:40 v/v) was obtained 6-[5-amino-3-phenyl-6-(2-phenylethoxy)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone as a solid (9 mg). By elution with a mixture of MeOH and EtOAc (1:99 v/v) was obtained 6-(5-amino-6-oxo-3-phenyl-1,6-dihydro-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone as a solid (89 mg).

Workup

  1. temperaturethe mixture was heated at 100-105° C. for 15 hours
  2. customan aqueous layer was removed by decantation
  3. customto give a residue
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography on silica gel
  7. washBy elution
  8. additionwith a mixture of n-hexane

Sources & evidence

ORD record
ord-be89647175e84225a49665147b157cd0
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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