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

HRID 340512Notes

Reaction equation

HRID 340512 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-91a3324b2a414780a29d7f7497b52254
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

Loading…