Cyanogen Bromide → 6-Chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

HRID 217692

Reaction equation

HRID 217692 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[C:4]([CH3:10])[CH:3]=1.[N:11]#[C:12][Br:13]>CCO.O>[BrH:13].[Cl:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]2[N:6]([C:12]([NH2:11])=[N:9][N:8]=2)[N:7]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 114464906-Chloro-3-hydrazinyl-4-methylpyridazine

Product 1

HCID 866507966-Chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

(6-Chloro-4-methylpyridazin-3-yl)hydrazine (W3.002; 4.6 g) were initially charged in EtOH (330 ml) and water (70 ml) while stirring at RT. Thereafter, cyanogen bromide in a mixture of EtOH (170 ml) and water (30 ml) was slowly added dropwise at RT. After stirring at RT for 6 h, the mixture was left to stand overnight. Then the mixture was dried and the residue was purified using silica gel (40 g cartridge, DCM/methanol gradient of 0-10% in 30 min). 7.3 g of the title compound were obtained.

Workup

  1. additionwas slowly added dropwise at RT
  2. waitthe mixture was left
  3. waitto stand overnight
  4. customThen the mixture was dried
  5. customthe residue was purified
  6. customsilica gel (40 g cartridge, DCM/methanol gradient of 0-10% in 30 min)

Sources & evidence

ORD record
ord-b4614576bfab4dd4b2399c21f7253d21
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Linked notes

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