Sulfuric Acid → HCID 178499175, compound

HRID 1463229Notes

Reaction equation

HRID 1463229 reaction equation
F[C:2](F)(F)C(O)=O.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]3[NH:21][N:22]=[C:23]([C:24]([OH:26])=[O:25])[C:18]3=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.OS(O)(=O)=O>CO>[CH3:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]2[N:20]=[C:19]3[NH:21][N:22]=[C:23]([C:24]([O:26][CH3:2])=[O:25])[C:18]3=[CH:17][CH:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178480628HCID 178480628, compound

Product 1

HCID 178499175HCID 178499175, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(4-Methyl-1-piperazinyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate trifluoroacetate (1.82 g, 4.8 mmole) was refluxed overnight in 300 mL of MeOH containing 2 mL of concentrated H2SO4. The reaction mixture was concentrated to ca. 100 mL and then distributed between EtOAc and an aqueous NaHCO3 solution. The aqueous phase was extracted additional two times with EtOAc and then the combined organic phase was dried and concentrated. Recrystallization from MeOH gave 1.21 g (91%) of analytically pure product, mp 230° -231° C.

Workup

  1. concentrationThe reaction mixture was concentrated to ca. 100 mL
  2. extractionThe aqueous phase was extracted additional two times with EtOAc
  3. customthe combined organic phase was dried
  4. concentrationconcentrated
  5. customRecrystallization from MeOH
  6. customgave 1.21 g (91%) of analytically pure product, mp 230° -231° C.

Sources & evidence

ORD record
ord-3913339f6f244de6b5ab28b29d2b584a
Source dataset
uspto-grants-1994_04
Patent number
US05300498

Reaction notes

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