HCID 15020538, compound → HCID 14823451, compound

HRID 1461830Notes

Reaction equation

HRID 1461830 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](S(C1C=CC=CC=1)(=O)=O)[N:7]=[C:6]2[N:21]1[CH2:26][CH2:25][N:24](C#N)[CH2:23][CH2:22]1.[Al].[Li].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 15020538HCID 15020538, compoundHCID 16211445Aluminum;lithiumHCID 21226445Aluminium lithium hydride

Product 1

HCID 14823451HCID 14823451, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 4-[5-methoxy-1-phenylsulfonyl-1H-indazol-3-yl]-1-piperazinecarbonitrile (9.5 g, 0.0239 mol) in THF (150 ml) under N2 was added, dropwise, lithium aluminum [50 ml (2.1 eq) of a 1M LiAlH4 solution in THF]. After complete addition the reaction was warmed to reflux and stirred for 3 hours. To the cooled reaction was added carefully, H2O (15 ml) to destroy the excess LiAlH4. The mixture was allowed to stand overnight. The reaction mixture was filtered through a coarse sintered glass funnel. The resultant cake was washed well with THF and the THF filtrate was concentrated to afford 6.0 g, of a residue. The residue was triturated with ether and H2O and the resultant solid was collected and dried to afford 4.5 g of 5-methoxy-3-(1-piperazinyl)-1H-indazole, m.p. 163°-169° C.

Workup

  1. additionwas added
  2. additionAfter complete addition the reaction
  3. temperaturewas warmed
  4. temperatureto reflux
  5. customTo the cooled reaction
  6. additionwas added carefully
  7. customH2O (15 ml) to destroy the excess LiAlH4
  8. waitto stand overnight
  9. filtrationThe reaction mixture was filtered through a coarse sintered glass funnel
  10. washThe resultant cake was washed well with THF
  11. concentrationthe THF filtrate was concentrated
  12. customto afford 6.0 g
  13. customThe residue was triturated with ether and H2O
  14. customthe resultant solid was collected
  15. customdried

Sources & evidence

ORD record
ord-cf1fafa2038c45e6b7e2c244f7dd2651
Source dataset
uspto-grants-1991_12
Patent number
US05077405

Reaction notes

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