Piperidine → 6-Piperidin-1-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 217674Notes

Reaction equation

HRID 217674 reaction equation
Br.Cl[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([NH2:12])=[N:10][N:11]=2)[N:8]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>O>[N:13]1([C:3]2[CH:4]=[CH:5][C:6]3[N:7]([C:9]([NH2:12])=[N:10][N:11]=3)[N:8]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 866507946-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

Product 1

HCID 151078826-Piperidin-1-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.001; 100 mg) were initially charged in water (1 ml) and admixed with piperidine (260 μl) with stirring. Thereafter, the mixture was heated to reflux for 1 h and, after cooling, freed of the solvent. Subsequently, the mixture was admixed with water and the solid formed was filtered off with suction and dried. The mother liquor was dried and admixed with a little water. The solid obtained was filtered off with suction and dried. The filtrate was then 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. The three resulting solid fractions were combined and gave rise to 56 mg of the title compound.

Workup

  1. temperatureThereafter, the mixture was heated
  2. temperatureto reflux for 1 h
  3. temperatureafter cooling, freed of the solvent
  4. customthe solid formed
  5. filtrationwas filtered off with suction
  6. customdried
  7. customThe mother liquor was dried
  8. customThe solid obtained
  9. filtrationwas filtered off with suction
  10. customdried
  11. extractionThe filtrate was then extracted three times with dichloromethane
  12. dry with materialThe combined organic phases were dried over sodium sulfate
  13. filtrationafter the desiccant had been filtered off
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-54e1cb8527cf46c4896cfb1e2f9d958f
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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