Hydrogen Peroxide → HCID 67453876, compound

HRID 869152Notes

Reaction equation

HRID 869152 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[N:13][C:12]([N:15]([CH2:23][C:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)([CH3:26])[CH3:25])C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)=[N:7][CH:8]=1)#[N:2].OO.C(=O)([O-])[O-:37].[K+].[K+].Cl.O1CCOCC1>O.C(OCC)(=O)C>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:24]([CH3:25])([CH3:26])[CH2:23][NH:15][C:12]2[N:13]=[N:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]([NH2:2])=[O:37])=[CH:8][N:7]=3)=[CH:10][CH:11]=2)=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 86686127HCID 86686127, compound

Product 1

HCID 67453876HCID 67453876, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 20 dram vial was added crude tert-butyl 6-(5-cyanopyridin-2-yl)pyridazin-3-yl(2-(4-fluorophenyl)-2-methylpropyl)carbamate, hydrogen peroxide (2 mL), and potassium carbonate (150 mg). The reaction was stirred for 30 min and then diluted with water (20 mL) and ethyl acetate (50 mL). After transferring to a separatory funnel and shaking, the organic layer was separated from the aqueous layer and then washed with brine (20 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was subsequently treated with 4N HCl/dioxane (1 mL). The reaction was stirred for 1 h at room temperature, concentrated, quenched with aqueous sodium bicarbonate, and extracted with ethyl acetate (20 mL). The organic layer was then dried (Na2SO4), filtered, and concentrated to give a crude solid that was purified by reverse phase column chromatography to afford 10 mg of 6-(6-(2-(4-fluorophenyl)-2-methylpropylamino)pyridazin-3-yl)nicotinamide, m/z=366.1 [M+H].

Workup

  1. customAfter transferring to a separatory funnel
  2. stirringshaking
  3. customthe organic layer was separated from the aqueous layer
  4. washwashed with brine (20 mL)
  5. dry with materialThe organic layer was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude solid that
  9. stirringThe reaction was stirred for 1 h at room temperature
  10. concentrationconcentrated
  11. customquenched with aqueous sodium bicarbonate
  12. extractionextracted with ethyl acetate (20 mL)
  13. dry with materialThe organic layer was then dried (Na2SO4)
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customto give a crude solid that
  17. customwas purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-66926d65bb134386bda27eee1bb28c35
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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