Triethylamine → HCID 10978418, compound

HRID 1169133Notes

Reaction equation

HRID 1169133 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=O)[N:10]=2)[N:7]=1.Cl.[CH3:18][NH:19][CH3:20].C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([CH3:16])([CH3:15])[C:12]([N:19]([CH3:20])[CH3:18])=[O:14])[N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11746720HCID 11746720, compound

Product 1

HCID 10978418HCID 10978418, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.959 g of 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionic acid was dissolved in 6 ml of N,N-dimethylformamide; 0.714 g of N,N′-carbonyldiimidazole was added, followed by stirring at room temperature for 60 minutes. To this mixture, 0.392 g of dimethylamine hydrochloride and 0.665 ml of triethylamine were added under ice cooling conditions, followed by stirring at room temperature for 3 hours. Saline was added to the reaction mixture, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate:methanol (95:5). The desired fraction was collected and concentrated; the crystal obtained was collected by filtration to yield 0.608 g of the title compound.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. additionSaline was added to the reaction mixture
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe extract was washed with saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with ethyl acetate:methanol (95:5)
  8. customThe desired fraction was collected
  9. concentrationconcentrated
  10. customthe crystal obtained
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ee0a4f90d425462ca0c99fd6fd3c8811
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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