Dimethylformamide → HCID 178453122, compound

HRID 219154Notes

Reaction equation

HRID 219154 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][N:11]=2)[N:8]=1)#[CH:2].[N-:21]=[N+:22]=[N-:23].[Na+].CN(C=O)C>O>[N:21]1[CH:2]=[C:1]([C:3]2[CH:4]=[CH:5][C:6]3[N:7]([C:9]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[N:10][N:11]=3)[N:8]=2)[NH:23][N:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 57691050tert-Butyl (6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 178453122HCID 178453122, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl (6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (0.109 g, 0.399 mmol) and sodium azide (0.0285 g, 0.439 mmol) were dissolved DMF (2 mL) at RT. The reaction mixture was stirred overnight at RT then at 70° C. for 3 h. Water was added at RT and the aqueous layer was extracted with EtOAc and 1-butanol. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. Used without further purification.

Workup

  1. waitat 70° C. for 3 h
  2. extractionthe aqueous layer was extracted with EtOAc and 1-butanol
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customUsed without further purification

Sources & evidence

ORD record
ord-8113e85c77754af58d90bc4bdeaa8200
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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