Ethyl Acetate → HCID 178509241, compound

HRID 334416Notes

Reaction equation

HRID 334416 reaction equation
ClC1C=CC=C(C(OO)=O)C=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23](SC)[N:22]=1.C(OCC)(=O)C.Cl.[NH2:38][NH2:39]>ClCCl.C(O)CC.O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[N:22]=[C:23]2[NH:38][N:39]=[C:25]([NH2:26])[C:24]2=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 115031Hydrazinium chlorideHCID 68276347HCID 68276347, compound

Product 1

HCID 178509241HCID 178509241, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Procedure

769 mg (3.12 mmol) of m-chloroperbenzoic acid (mCPBA) is added under argon to a stiring solution of 786 mg (2.83 mmol) of 6-(2,4-difluorophenylamino)-2-(methylthio)nicotinonitrile in 25 mL of dichloromethane. The reaction medium is stirred 1 hour at room temperature before adding a fraction of ethyl acetate and washed this organic phase with a NaHCO3 saturated solution. The combined organic phases are dried on magnesium sulfate and dry evaporated. The crude reaction product is dissolved again in 10 mL of propanol and 2 equivalents of hydrazine hydrochloride in water are 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 495 mg of N6-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridine-3,6-diamine in the form of a yellow-orange solid (67%).

Workup

  1. washwashed this organic phase with a NaHCO3 saturated solution
  2. customThe combined organic phases are dried 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-e29503f9d2d841c1aa8372286e7f20a9
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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