Hydrogen Peroxide → 6-((2R)-1-amino-4-methyl-1-oxopentan-2-ylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide

HRID 1620119Notes

Reaction equation

HRID 1620119 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].OO.[C:9]([C:11]1[CH:12]=[C:13]([F:37])[C:14]([NH:28][C@H:29]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:30]([NH2:32])=[O:31])=[N:15][C:16]=1[NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2)#[N:10].[Cl-].[Na+]>C(OCC)(=O)C.O.C(O)C>[NH2:32][C:30](=[O:31])[C@H:29]([NH:28][C:14]1[C:13]([F:37])=[CH:12][C:11]([C:9]([NH2:10])=[O:2])=[C:16]([NH:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)[N:15]=1)[CH2:33][CH:34]([CH3:35])[CH3:36]

Participants

8

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 86683890(2R)-2-(5-cyano-3-fluoro-6-(quinolin-6-ylamino)pyridin-2-ylamino)-4-methylpentanamide

Product 1

HCID 677768506-((2R)-1-amino-4-methyl-1-oxopentan-2-ylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamideYield 38.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (35 mg) and a 30% hydrogen peroxide solution (29 μl) were added to an ethanol (1 ml) solution containing (2R)-2-(5-cyano-3-fluoro-6-(quinolin-6-ylamino)pyridin-2-ylamino)-4-methylpentanamide (20 mg), followed by stirring at room temperature for 1 hour. A 30% hydrogen peroxide solution (29 μl) was added to the reaction mixture, followed by stirring at room temperature for 1 hour. Water, sodium chloride, and ethyl acetate were added to the reaction mixture. The organic layer was collected and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was dissolved in ethyl acetate, and diisopropylether was added. Solid matter was collected by filtration and washed with diisopropylether, and a yellow solid of 6-((2R)-1-amino-4-methyl-1-oxopentan-2-ylamino)-5-fluoro-2-(quinolin-6-ylamino)nicotinamide (8 mg) was thus obtained.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. dissolutionThe obtained residue was dissolved in ethyl acetate
  6. additiondiisopropylether was added
  7. filtrationSolid matter was collected by filtration
  8. washwashed with diisopropylether

Sources & evidence

ORD record
ord-98a181a4f3d046318fda9b05d71dc6d1
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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