Hydrazine hydrate (1:1) → (2-Ethyl-2H-indazol-5-yl)methanamine

HRID 73079Notes

Reaction equation

HRID 73079 reaction equation
[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][N:13]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:9]2)=[N:4]1)[CH3:2].NN.O>CO>[CH2:1]([N:3]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][NH2:13])=[CH:9]2)=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 668378912-((2-Ethyl-2H-indazol-5-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 66837823(2-Ethyl-2H-indazol-5-yl)methanamineYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-((2-ethyl-2H-indazol-5-yl)methyl)isoindoline-1,3-dione (step-3 of Example 13, mixture) in MeOH (7 mL) was added hydrazine-H2O (0.5 mL), and the mixture was heated at 50° C. for 4 hrs. The mixture was concentrated, the residual white solid was added 2 M aqueous NaOH, and extracted with DCM, dried over Na2SO4, filtered and concentrated. The residual oil was diluted with MeOH and applied onto a strong cation exchange cartridge (BondElute (registered trademark) SCX, 1 g/6 mL, Varian Inc.), and the solid phase matrix was rinsed with MeOH (6 mL). The crude mixture was eluted with 1 M NH3 in MeOH (6 mL) and concentrated to give 68 mg (52% yield in 2 steps) of the titled compound as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residual white solid was added 2 M aqueous NaOH
  3. extractionextracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe residual oil was diluted with MeOH
  8. washthe solid phase matrix was rinsed with MeOH (6 mL)
  9. washThe crude mixture was eluted with 1 M NH3 in MeOH (6 mL)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-788f0d62af2e41c9a3933edaf210dfee
Source dataset
uspto-grants-2014_09
Patent number
US08829026B2

Reaction notes

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