Diethylamine → N*6*,N*6*-Diethyl-[1,2,4]triazolo[4,3-b]pyridazine-3,6-diamine

HRID 217675Notes

Reaction equation

HRID 217675 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.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14]>O>[CH2:13]([N:15]([CH2:16][CH3:17])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([NH2:12])=[N:10][N:11]=2)[N:8]=1)[CH3:14]

Participants

4

Reactant 2

HCID 8021Diethylamine2×HCID 866507946-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

Product 1

HCID 58136803N*6*,N*6*-Diethyl-[1,2,4]triazolo[4,3-b]pyridazine-3,6-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.001; 150 mg) was initially charged in water (5 ml) and admixed with diethylamine (814 μl) while stirring. Thereafter, the mixture was heated to reflux for 16 h and then further diethylamine (407 μl) was added. After refluxing for a further 12 h, the mixture was freed of the solvent, 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. 67 mg of the title compound were obtained.

Workup

  1. temperatureThereafter, the mixture was heated
  2. temperatureto reflux for 16 h
  3. temperatureAfter refluxing for a further 12 h
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationafter the desiccant had been filtered off
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-6ae71a2a14fd41f982d85b08818a25cc
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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