1-Butanol → HCID 69331965, compound

HRID 915077Notes

Reaction equation

HRID 915077 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][CH3:6].[NH2:8][C:9]1[N:10]=[C:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:12]([C:19]2[CH:20]=[CH:21][C:22](=[O:28])[N:23]([CH:25]([CH3:27])[CH3:26])[N:24]=2)=[N:13][C:14]=1S(C)(=O)=O.Cl>CCCCCC>[NH2:8][C:9]1[N:10]=[C:11]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:12]([C:19]2[CH:20]=[CH:21][C:22](=[O:28])[N:23]([CH:25]([CH3:27])[CH3:26])[N:24]=2)=[N:13][C:14]=1[O:7][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69331470HCID 69331470, compound

Product 1

HCID 69331965HCID 69331965, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

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 to 1-butanol (0.0716 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. After addition of 0.1N HCl (3 ml) was added to the mixture and a precipitate was collected by filtration. The precipitate was dissolved in CHCl3, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (80:20 v/v) to give a solid. The solid was suspended in hexane and collected by filtration to give 6-(5-amino-6-butoxy-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (83 mg).

Workup

  1. temperaturethe mixture was heated at 100-105° C. for 15 hours
  2. additionwas added to the mixture
  3. filtrationa precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in CHCl3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (80:20 v/v)
  8. customto give a solid
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b377ae83d57b4132a3a897f38f168fca
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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