Triethylamine → HCID 23153704, compound

HRID 1990784Notes

Reaction equation

HRID 1990784 reaction equation
C(N(CC)CC)C.CC[C:10]([C:12](Cl)=[O:13])=O.[NH:15]([C:17]1[N:18]=[N:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[CH:21][CH:22]=1)[NH2:16].[O:31]1CCO[CH2:33][CH2:32]1>>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH:21]=[CH:22][C:17]3[N:18]([C:33]([C:32]([O:13][CH2:12][CH3:10])=[O:31])=[N:16][N:15]=3)[N:19]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 11007880Butanoyl chloride, 2-oxo-HCID 157438723-Hydrazinyl-6-(4-methoxyphenyl)pyridazine

Product 1

HCID 23153704HCID 23153704, compoundYield 21%

Conditions

Temperature
60 °C

Procedure

2.09 ml (15.0 mmol) of triethylamine and 1.23 ml (11.0 mmol) of ethyloxalyl chloride were added to a dioxane solution (20 ml) of 2.16 g (10.0 mmol) of 3-hydrazino-6-(4-methoxyphenyl)pyridazine, obtained according to the method described in Journal of Medicinal Chemistry, Vol. 30, pp. 239-249 (1987), and the reaction liquid was stirred at 60° C. for 4 hours. The reaction liquid was concentrated under reduced pressure, and acetic acid (10 ml) was added to the resulting residue and stirred at 120° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/4) to obtain 615 mg (yield: 21%) of ethyl 6-(4-methoxyphenyl)[1,2,4]triazolo[4,3-b]pyridazine-3-carboxylate.

Workup

  1. customobtained
  2. custom239-249 (1987), and the reaction liquid
  3. customThe reaction liquid
  4. concentrationwas concentrated under reduced pressure, and acetic acid (10 ml)
  5. additionwas added to the resulting residue
  6. stirringstirred at 120° C. for 2 hours
  7. customThe reaction liquid
  8. concentrationwas concentrated under reduced pressure
  9. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=1/4)

Sources & evidence

ORD record
ord-b05095c0c7b343af842cd95d6f3aef19
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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