2-Fluoro-6-(4-methyl-1-piperazinyl)pyridine-3-carboxaldehyde acetylhydrazone → 1-Methyl-6-(4-methyl-1-piperazinyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1463227Notes

Reaction equation

HRID 1463227 reaction equation
[C:1]([NH:4][N:5]=[CH:6][C:7]1[C:8](F)=[N:9][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:11][CH:12]=1)(=O)C>CNN>[CH3:1][N:4]1[C:8]2=[N:9][C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)=[CH:11][CH:12]=[C:7]2[CH:6]=[N:5]1

Participants

3

Reactant 1

HCID 541133102-Fluoro-6-(4-methyl-1-piperazinyl)pyridine-3-carboxaldehyde acetylhydrazone

Product 1

HCID 108234221-Methyl-6-(4-methyl-1-piperazinyl)-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6061MethylhydrazineSolvent

Procedure

2-Fluoro-6-(4-methyl-1-piperazinyl)pyridine-3-carboxaldehyde acetylhydrazone (2.30 g, 8.23 mmole) was warmed at 90° C. in 10 mL of methylhydrazine. After 30 minutes the reaction mixture was concentrated under reduced pressure and the resulting solid triturated with water. The product was filtered off and the aqueous filtrate was extracted three times with CH2Cl2. The CH2Cl2 was evaporated and the residual product was combined with the product that had been previously filtered off and the two were recrystallized together from pentane, giving 1.37 g (72%), mp 106°-107° C.

Workup

  1. concentrationAfter 30 minutes the reaction mixture was concentrated under reduced pressure
  2. customthe resulting solid triturated with water
  3. filtrationThe product was filtered off
  4. extractionthe aqueous filtrate was extracted three times with CH2Cl2
  5. customThe CH2Cl2 was evaporated
  6. filtrationhad been previously filtered off
  7. customthe two were recrystallized together from pentane
  8. customgiving 1.37 g (72%), mp 106°-107° C.

Sources & evidence

ORD record
ord-16fbc2f4740b4d84a43f355afb0bc9cc
Source dataset
uspto-grants-1994_04
Patent number
US05300498

Reaction notes

Loading…