HCID 68277390, compound → HCID 178480756, compound

HRID 1487411Notes

Reaction equation

HRID 1487411 reaction equation
C([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([S:14][C:15]3[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=3)[CH:13]=[C:8]2[C:7]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)=[O:25])=[N:6]1)(C)(C)C>FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>[F:21][C:19]1[CH:20]=[C:15]([S:14][C:12]2[CH:13]=[C:8]3[C:7]([NH:23][C:24]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)=[CH:29][CH:28]=4)=[O:25])=[N:6][NH:5][C:9]3=[N:10][CH:11]=2)[CH:16]=[C:17]([F:22])[CH:18]=1

Participants

4

Reactant 1

HCID 68277390HCID 68277390, compound

Product 1

HCID 178480756HCID 178480756, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 0.150 g (0.272 mmol) of 1-(1-tert-butyl-5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-(4-(4-methylpiperazin-1-yl)phenyl)urea dissolved in 20 ml of TFA (trifluoroacetic acid) is refluxed for 3 hours. The solvent is evaporated and the crude reaction product is diluted with saturated NaHCO3 solution and extracted with ethyl acetate. The organic phase is dried on MgSO4, filtered and concentrated. The solid obtained is triturated in methanol, filtered and dried. 110 mg (82%) of 1-(5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-(4-(4-methylpiperazin-1-yl)phenyl)urea in the form of a beige solid is obtained.

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe solvent is evaporated
  3. customthe crude reaction product
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried on MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe solid obtained
  9. customis triturated in methanol
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-845ecb66d44b4d0eb3213f684a2b8277
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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