Water → HCID 58045962, compound

HRID 657884Notes

Reaction equation

HRID 657884 reaction equation
Cl[C:2]1[C:3]([CH:15]2[CH2:17][CH2:16]2)=[C:4]([CH:12]2[CH2:14][CH2:13]2)[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1.[O-:18][CH2:19][CH3:20].[Na+].O>C(O)C>[CH:15]1([C:3]2[C:2]([O:18][CH2:19][CH3:20])=[N:7][N:6]3[C:8]([NH2:11])=[N:9][N:10]=[C:5]3[C:4]=2[CH:12]2[CH2:14][CH2:13]2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 58045986HCID 58045986, compound

Product 1

HCID 58045962HCID 58045962, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-7,8-dicyclopropyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.016, 0.1 g) was dissolved in ethanol (20 ml) while stirring and under argon. Thereafter, the reaction mixture was admixed with sodium ethoxide (110 mg) and stirred at RT for 1 h, then at 55° C. for 1 h. Subsequently, the mixture was left to stand overnight and then heated to reflux for 7.5 h. After standing over the weekend, the solvent was drawn off, and the residue was admixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 100 mg of the title compound were obtained.

Workup

  1. stirringstirred at RT for 1 h
  2. waitSubsequently, the mixture was left
  3. waitto stand overnight
  4. temperatureheated
  5. temperatureto reflux for 7.5 h
  6. extractionextracted three times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationafter the desiccant had been filtered off
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-03851658f5554eb1964ffcff9985550b
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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