Cyanogen Bromide → 6-Chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide

HRID 1524501Notes

Reaction equation

HRID 1524501 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].[N:12]#[C:13][Br:14]>CCO.O>[BrH:14].[Cl:1][C:2]1[C:3]([CH3:11])=[C:4]([CH3:10])[C:5]2[N:6]([C:13]([NH2:12])=[N:9][N:8]=2)[N:7]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 126480423-Chloro-6-hydrazinyl-4,5-dimethylpyridazine

Product 1

HCID 866507976-Chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromideYield 100.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

(6-Chloro-4,5-dimethylpyridazin-3-yl)hydrazine (W3.006; 12 g) was initially charged in EtOH (240 ml) and water (50 ml) while stirring at RT. Thereafter, cyanogen bromide (14.7 g) in a mixture of EtOH (120 ml) and water (25 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 (80 g cartridge, DCM/methanol gradient of 0-20% in 60 min). 19.4 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 (80 g cartridge, DCM/methanol gradient of 0-20% in 60 min)

Sources & evidence

ORD record
ord-770df7b676fd4cb9b4008a42023db1f0
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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