1,4-Dioxane → HCID 23057947, compound

HRID 346512Notes

Reaction equation

HRID 346512 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[N:12]=3)=[N:9][N:10]=2)[N:7]=1.O1[CH2:23][CH2:22]OCC1>>[N:6]1([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[N:12]=4)=[N:9][N:10]=3)[N:7]=2)[CH2:23][CH2:22][CH2:14][CH2:15][CH2:16][CH2:11][CH2:8]1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 23057944HCID 23057944, compound

Product 1

HCID 23057947HCID 23057947, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 6-chloro-3-(6-chloropyridin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine (620 mg), heptamethylenimine (1.32 g) and 1,4-dioxane (20 ml) was stirred at 100° C. for 9 hours. After allowing to cool to room temperature, the reaction solution was concentrated under reduced pressure, and the resultant residue was extracted with ethyl acetate. The extract was washed successively with 5% aqueous solution of citric acid, water, saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant crude crystal was recrystallized from ethanol, to obtain 6-azocan-1-yl -3-(6-chloropyridin-2-yl)-1,2,4-triazolo[4,3-b]pyridazine (370 mg) as grayish white crystals.

Workup

  1. temperatureto cool to room temperature
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. extractionthe resultant residue was extracted with ethyl acetate
  4. washThe extract was washed successively with 5% aqueous solution of citric acid, water, saturated aqueous solution of sodium hydrogen carbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-2571f2ac621549bc8747bd408ef3e3b7
Source dataset
uspto-grants-2007_02
Patent number
US07173033B2

Reaction notes

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