Hydrazine hydrate (1:1) → HCID 67362732, compound

HRID 2174536Notes

Reaction equation

HRID 2174536 reaction equation
C[N:2](C)[C:3]1[CH:8]=[N:7][N:6]([CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[C:5](=[O:19])[C:4]=1[CH:20]=O.[NH2:23]N.O>CCO>[CH3:18][C:11]1([CH3:17])[CH2:12][C:13]([CH3:15])([CH3:16])[CH2:14][CH:9]([N:6]2[C:5](=[O:19])[C:4]3[CH:20]=[N:23][NH:2][C:3]=3[CH:8]=[N:7]2)[CH2:10]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86677513HCID 86677513, compound

Product 1

HCID 67362732HCID 67362732, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-dimethylamino-3-oxo-2-(3,3,5,5-tetramethyl-cyclohexyl)-2,3-dihydro-pyridazine-4-carbaldehyde (1.19 g, 3.903 mmol) in EtOH (30 mL) was treated with H2NNH2.H2O (1.2 mL, 39.03 mmol). After stirring at reflux for 20 h, the volatiles were removed in vacuo and the solid residue was extracted with EtOAc. The organics were then washed with brine, dried (Na2SO4). After evaporation of volatiles, the residue was purified by flash chromatography (50 g (solute SiO2 cartridge, continuous gradient 100% hexanes→hexanes/EtOAc, 1:1) to provide 5-(3,3,5,5-tetramethyl-cyclohexyl)-1,5-dihydro-pyrazolo[3,4-d]pyridazin-4-one (495.3 mg, 46%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.36 (1H, s), 8.31 (1H, s), 5.45 (1H, app heptet, J=4.6 Hz), 1.71-1.57 (4H, m), 1.40-1.22 (2H, m), 1.19 (6H, s), 1.00 (6H, s).

Workup

  1. temperatureat reflux for 20 h
  2. customthe volatiles were removed in vacuo
  3. extractionthe solid residue was extracted with EtOAc
  4. washThe organics were then washed with brine
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of volatiles
  7. customthe residue was purified by flash chromatography (50 g (solute SiO2 cartridge, continuous gradient 100% hexanes→hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-0003183cfc7c4125a1ad17053ff59ce0
Source dataset
uspto-grants-2015_06
Patent number
US09062004B2

Reaction notes

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