Ethyl Acetate → HCID 178482076, compound

HRID 334417Notes

Reaction equation

HRID 334417 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[N:20]([CH3:31])[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23](SC)[N:22]=1.C(OCC)(=O)C.Cl.[NH2:39][NH2:40]>ClCCl.C(O)CC.O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[N:20]([CH3:31])[C:21]1[N:22]=[C:23]2[NH:39][N:40]=[C:25]([NH2:26])[C:24]2=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 115031Hydrazinium chlorideHCID 68276399HCID 68276399, compound

Product 1

HCID 178482076HCID 178482076, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Procedure

452 mg (1.84 mmol) of mCPBA is added under argon to a stirring solution of 486 mg (1.67 mmol) of 6-((2,4-difluorophenyl)(methyl)amino)-2-(methylthio)nicotinonitrile in 15 mL of dichloromethane. The reaction medium is stirred 30 min at room temperature before adding an ethyl acetate fraction. The organic phase is washed with a NaHCO3 saturated solution, dried on magnesium sulfate and dry evaporated. The crude reaction product is dissolved again in 6 mL of propanol and 164 μL (3.38 mmol) of hydrazine hydrochloride in water is added. The mixture is heated at 90° C. for 6 hours before being diluted in water and extracted with ethyl acetate. The organic phase is dried on magnesium sulfate and dry evaporated before being purified by silica gel chromatography to yield 328 mg of N6-(2,4-difluorophenyl)-N6-methyl-1H-pyrazolo[3,4-b]pyridine-3,6-diamine in the form of a yellow-orange solid (70%).

Workup

  1. washThe organic phase is washed with a NaHCO3 saturated solution
  2. customdried on magnesium sulfate
  3. customdry
  4. customevaporated
  5. customThe crude reaction product
  6. temperatureThe mixture is heated at 90° C. for 6 hours
  7. extractionextracted with ethyl acetate
  8. customThe organic phase is dried on magnesium sulfate
  9. customdry
  10. customevaporated
  11. custombefore being purified by silica gel chromatography

Sources & evidence

ORD record
ord-73d275e6856643aeae058cb2eec22f5b
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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