1-(Benzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indazole → 3-(4-Methylpiperazin-1-yl)-1H-indazole

HRID 1637985Notes

Reaction equation

HRID 1637985 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10](S(C3C=CC=CC=3)(=O)=O)[N:9]=2)[CH2:4][CH2:3]1.CO[Na]>CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 148234251-(Benzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indazoleHCID 178418582HCID 178418582, compound

Product 1

HCID 148234523-(4-Methylpiperazin-1-yl)-1H-indazoleYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A stirred mixture of 3-(4-methyl-1-piperazinyl)-1-phenylsulfonyl-1H-indazole (13.5 g, 38 mmol), methanol (150 ml) and 25% CH3ONa in methanol (15.3 ml) was stirred and refluxed for 2.5 hours. The reaction was concentrated to about one-tenth its volume, and water was added to the mixture, resulting in a red solution. The solution was extracted with dichloromethane, the extract washed (H2O), dried (MgSO4), and the solvent was concentrated to afford 6.6 g of a rose-colored solid. Two recrystallizations from toluenehexane afforded 4.3 g (52%) of 3-(4-methyl-1-piperazinyl)-1H-indazole as an off-white solid, m.p.=111-113° C.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. concentrationThe reaction was concentrated to about one-tenth its volume, and water
  3. additionwas added to the mixture
  4. customresulting in a red solution
  5. extractionThe solution was extracted with dichloromethane
  6. washthe extract washed (H2O)
  7. dry with materialdried (MgSO4)
  8. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-6a8ff4c7fe8d40099f1b751465213688
Source dataset
uspto-grants-2000_03
Patent number
US06043240

Reaction notes

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