Hydrogen Peroxide → HCID 117643709, compound

HRID 2171285Notes

Reaction equation

HRID 2171285 reaction equation
[OH-].[Na+].OO.CS(C)=O.CC[OH:11].[ClH:12].[C:13]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23]2[C:30]([F:31])=[CH:29][C:26]([C:27]#[N:28])=[C:25]([NH:32][C:33]3[CH:34]=[N:35][CH:36]=[C:37]([CH3:39])[CH:38]=3)[N:24]=2)[CH:18]([NH2:40])[CH2:17]1)(=[O:15])[CH3:14]>O>[ClH:12].[C:13]([N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23]2[C:30]([F:31])=[CH:29][C:26]([C:27]([NH2:28])=[O:11])=[C:25]([NH:32][C:33]3[CH:34]=[N:35][CH:36]=[C:37]([CH3:39])[CH:38]=3)[N:24]=2)[CH:18]([NH2:40])[CH2:17]1)(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22338741Dimethylsulfoxide ethanolHCID 117644363HCID 117644363, compound

Product 1

HCID 117643709HCID 117643709, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5M sodium hydroxide aqueous solution (0.038 ml) and a 30% hydrogen peroxide solution (0.008 ml) were added to a DMSO/EtOH (0.1 ml/0.1 ml) solution containing 6-((1-acetyl-3-aminopiperidin-4-yl)amino)-5-fluoro-2-((5-methylpyridin-3-yl)amino)nicotinonitrile hydrochloride (6 mg), followed by stirring at room temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. Ethyl acetate (0.5 ml) and 4M hydrochloric acid/1,4-dioxane (0.004 ml) were added to the obtained residue, followed by stirring at room temperature for 0.5 hours. The solvent was removed under reduced pressure. The obtained residue was washed with ethyl acetate. A yellow solid of 6-((1-acetyl-3-aminopiperidin-4-yl)amino)-5-fluoro-2-((5-methylpyridin-3-yl)amino)nicotinamide hydrochloride (3.2 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layers were washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. additionEthyl acetate (0.5 ml) and 4M hydrochloric acid/1,4-dioxane (0.004 ml) were added to the obtained residue
  6. stirringby stirring at room temperature for 0.5 hours
  7. customThe solvent was removed under reduced pressure
  8. washThe obtained residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-3f82ee0c994b4c28a6ac9f140e8074c9
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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