Methanol → HCID 178509237, compound

HRID 1487416Notes

Reaction equation

HRID 1487416 reaction equation
[OH:1]OS([O-])=O.[K+].[F:7][C:8]1[CH:9]=[C:10]([S:15][C:16]2[CH:17]=[C:18]3[C:24]([NH2:25])=[N:23][NH:22][C:19]3=[N:20][CH:21]=2)[CH:11]=[C:12]([F:14])[CH:13]=1.O1CCCC1.CO.[OH2:33]>>[F:7][C:8]1[CH:9]=[C:10]([S:15]([C:16]2[CH:17]=[C:18]3[C:24]([NH2:25])=[N:23][NH:22][C:19]3=[N:20][CH:21]=2)(=[O:1])=[O:33])[CH:11]=[C:12]([F:14])[CH:13]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfite2×HCID 178509236HCID 178509236, compound

Product 1

HCID 178509237HCID 178509237, compoundYield 81%

Procedure

A solution of 663 mg (1.078 mmol) of oxone in 1.1 ml of water is added to a solution of 300 mg (1.078 mmol) of 5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-amine in 10 ml of a 1:1 mixture of tetrahydrofuran and methanol at 0° C. The reaction mixture is stirred at room temperature for 16 hours. An additional portion of 663 mg of oxone at 0° C. is then added and the reaction medium stirred at room temperature for 24 hours. The solvents are evaporated and the reaction medium is diluted with sodium bicarbonate solution, extracted with ethyl acetate, dried on MgSO4 and then concentrated to yield 340 mg (81%) of 5-(3,5-difluorophenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-3-amine in the form of a yellow solid.

Workup

  1. stirringthe reaction medium stirred at room temperature for 24 hours
  2. customThe solvents are evaporated
  3. additionthe reaction medium is diluted with sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. customdried on MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9b6a447e7cde4685a5544bc0592a4a99
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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