Hydrogen Peroxide → HCID 57486807, compound

HRID 1911735Notes

Reaction equation

HRID 1911735 reaction equation
[CH:1]1([CH2:6][N:7]([CH2:38][CH3:39])[C:8]2[N:13]=[C:12]3[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][C:9]=2[CH2:19][N:20]([CH2:23][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)[C:21]#[N:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:40]O.[OH-].[K+].O>C(O)C>[F:33][C:30]([F:31])([F:32])[C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([C:34]([F:35])([F:36])[F:37])[CH:27]=1)[CH2:23][N:20]([CH2:19][C:9]1[CH:10]=[C:11]2[C:16]([CH3:17])=[N:15][N:14]([CH3:18])[C:12]2=[N:13][C:8]=1[N:7]([CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH2:38][CH3:39])[C:21]([NH2:22])=[O:40]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14797Potassium HydroxideHCID 57486808HCID 57486808, compound

Product 1

HCID 57486807HCID 57486807, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of [6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-ylmethyl-(3,5-bis-trifluoromethyl-benzyl)-cyanamide (0.50 g, 0.880 mmol) in ethanol (15 mL) were added H2O2 (1.5 mL) and a saturated aqueous solution of KOH (0.70 g, 11.97 mmol) at 0° C. This mixture was slowly heated to reflux. After 2 h the reaction mixture was cooled to RT, water (10 mL) was added, and the product was extracted with ethyl acetate (3×40 mL). The combined organic layers were dried over sodium sulfate and evaporated to yield the crude residue. The crude was purified by column chromatography over 100-200 mesh silica gel using 10% ethyl acetate and petroleum ether to yield the title compound as a sticky oil (yield: 60%).

Workup

  1. customat 0° C
  2. temperatureThis mixture was slowly heated to reflux
  3. extractionthe product was extracted with ethyl acetate (3×40 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated
  6. customto yield the crude residue
  7. customThe crude was purified by column chromatography over 100-200 mesh silica gel using 10% ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-2b20574ca0014abd8af9a45b3d9665f4
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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