Methanol → 6,8-Dimethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 1524488Notes

Reaction equation

HRID 1524488 reaction equation
Cl[C:2]1[CH:3]=[C:4](S(C)(=O)=O)[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1.[CH3:16][O-:17].[Na+].[CH3:19][OH:20]>>[CH3:16][O:17][C:2]1[CH:3]=[C:4]([O:20][CH3:19])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 580458006-Chloro-8-methanesulfonyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Product 1

HCID 580459416,8-Dimethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Procedure

6-Chloro-8-methanesulfonyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.126; 100 mg, 0.40 mmol) was dissolved in methanol (10 ml), and sodium methoxide solution (0.75 ml, 4.04 mmol) was added. The mixture was heated to reflux for 3 h, then concentrated, and the residue was dissolved in water and a pH of 6 was established by adding aqueous hydrochloric acid. The mixture was extracted with EA and the combined organic phases were dried and concentrated. The remaining residue was purified by flash chromatography (dichloromethane:MeOH). Yield: 30 mg

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in water
  5. additionby adding aqueous hydrochloric acid
  6. extractionThe mixture was extracted with EA
  7. customthe combined organic phases were dried
  8. concentrationconcentrated
  9. customThe remaining residue was purified by flash chromatography (dichloromethane:MeOH)

Sources & evidence

ORD record
ord-ec74a36c2fb146079fb36d074a196fd2
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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