Ethyl orthoformate → 4-chloro-7-ethyl-7H-imidazo(4,5-c)pyridazine

HRID 1846001Notes

Reaction equation

HRID 1846001 reaction equation
[Cl:1][C:2]1[C:3]([NH2:11])=[C:4]([NH:8][CH2:9][CH3:10])[N:5]=[N:6][CH:7]=1.[CH2:12](OC(OCC)OCC)C>>[Cl:1][C:2]1[C:3]2[N:11]=[CH:12][N:8]([CH2:9][CH3:10])[C:4]=2[N:5]=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 867232305-Chloro-N3-ethyl-3,4-pyridazinediamine

Product 1

HCID 552967654-chloro-7-ethyl-7H-imidazo(4,5-c)pyridazineYield 45%

Procedure

A mixture of 5-chloro-N3-ethyl-pyridazine-3,4-diamine (Preparation 7, 10.0 g, 58 mmol) and triethylorthoformate (60 mL) were heated to reflux for 4 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in EtOAc (50 mL) and filtered. The filter cake was washed with EtOAc and then the organic layers were washed with saturated brine solution, dried over Na2SO4 and concentrated in vacuo to afford the title compound as a yellow solid in 45% yield, 4.8 g.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in EtOAc (50 mL)
  5. filtrationfiltered
  6. washThe filter cake was washed with EtOAc
  7. washthe organic layers were washed with saturated brine solution
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9682482d34b54dac85b63bf0e39d2623
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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