Ethanol → 6,8-Diethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 1524487Notes

Reaction equation

HRID 1524487 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.[O-:16][CH2:17][CH3:18].[Na+].[CH2:20]([OH:22])[CH3:21]>>[CH2:17]([O:16][C:2]1[CH:3]=[C:4]([O:22][CH2:20][CH3:21])[C:5]2[N:6]([C:8]([NH2:11])=[N:9][N:10]=2)[N:7]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 580458006-Chloro-8-methanesulfonyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Product 1

HCID 580459396,8-Diethoxy-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

Conditions

Temperature
50 °C

Procedure

6-Chloro-8-methanesulfonyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.126; 60 mg, 0.24 mmol) was dissolved in ethanol (5 ml), sodium ethoxide (500 μl, 21% in ethanol) was added and the mixture was heated to 50° C. for 5 h. The mixture was concentrated and the residue was purified by flash chromatography (dichloromethane:methanol). Yield: 54 mg LC-MS rt: 0.52 min [M+H]+: 224.1 (met. b)

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography (dichloromethane:methanol)
  3. customYield: 54 mg LC-MS rt
  4. custom0.52 min [M+H]+

Sources & evidence

ORD record
ord-09d6f58dc79e4784b80a22ef10ed7103
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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