Water → 6-(4-Methyl-1-piperazinyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1463226Notes

Reaction equation

HRID 1463226 reaction equation
C([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.O>O.NN>[CH3:19][N:16]1[CH2:17][CH2:18][N:13]([C:10]2[N:9]=[C:8]3[NH:4][N:5]=[CH:6][C:7]3=[CH:12][CH:11]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 962WaterHCID 541133102-Fluoro-6-(4-methyl-1-piperazinyl)pyridine-3-carboxaldehyde acetylhydrazone

Product 1

HCID 106088136-(4-Methyl-1-piperazinyl)-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

2-Fluoro-6-(4-methyl-1-piperazinyl)pyridine-3-carboxaldehyde acetylhydrazone (2.30 g, 8.23 mmole) was warmed at 90° C. in 20 mL of hydrazine hydrate. After 30 minutes, water was added to the reaction mixture and the product was filtered off. The aqueous filtrate was concentrated under reduced pressure and the resulting solid triturated with water. This product was combined with the product that had been previously filtered off and the two were recrystallized together from EtOAc, giving 1.15 g, (64%), mp 196°-197° C.

Workup

  1. filtrationthe product was filtered off
  2. concentrationThe aqueous filtrate was concentrated under reduced pressure
  3. customthe resulting solid triturated with water
  4. filtrationhad been previously filtered off
  5. customthe two were recrystallized together from EtOAc
  6. customgiving 1.15 g, (64%), mp 196°-197° C.

Sources & evidence

ORD record
ord-cd1f5161bd004347973ee9b67f15c2ef
Source dataset
uspto-grants-1994_04
Patent number
US05300498

Reaction notes

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