Hydrochloric Acid → HCID 69331901, compound

HRID 915076Notes

Reaction equation

HRID 915076 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[NH2:10][C:11]1[N:12]=[C:13]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:14]([C:21]2[CH:22]=[CH:23][C:24](=[O:30])[N:25]([CH:27]([CH3:29])[CH3:28])[N:26]=2)=[N:15][C:16]=1S(C)(=O)=O.Cl>CC(N(C)C)=O.C(Cl)(Cl)Cl>[NH2:10][C:11]1[N:12]=[C:13]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:14]([C:21]2[CH:22]=[CH:23][C:24](=[O:30])[N:25]([CH:27]([CH3:29])[CH3:28])[N:26]=2)=[N:15][C:16]=1[O:9][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 69331470HCID 69331470, compound

Product 1

HCID 69331901HCID 69331901, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a suspension of NaH (60% in oil suspension) (31.1 mg) in DMA (0.6 ml) was added cyclohexanol (0.081 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 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 eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give a solid. The solid was crystallized from a mixture of acetone and n-hexane (60:40 v/v) to give 6-[5-amino-6-(cyclohexyloxy)-3-phenyl-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (55 mg).

Workup

  1. temperaturethe mixture was heated at 100-105° C. for 15 hours
  2. additionwas added to the mixture
  3. customan aqueous layer was removed by decantation
  4. customto give a residue
  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 (60:40 v/v)
  8. customto give a solid
  9. customThe solid was crystallized from a mixture of acetone and n-hexane (60:40 v/v)

Sources & evidence

ORD record
ord-8fc3dab2a3d8415cb4532dbd45e8a593
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

Loading…