Hydrochloric Acid → HCID 10922198, compound

HRID 1169134Notes

Reaction equation

HRID 1169134 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](O)=[O:13])[N:10]=2)[N:7]=1.[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([CH3:16])([CH3:15])[CH2:12][OH:13])[N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 169536Tetrabutylammonium borohydrideHCID 11746720HCID 11746720, compound

Product 1

HCID 10922198HCID 10922198, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.719 g of 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropionic acid was dissolved in 15 ml of tetrahydrofuran; 0.535 g of N,N′-carbonyldiimidazole was added, followed by stirring at room temperature for 60 minutes. To this mixture, 1.15 g of tetra-n-butylammonium borohydride was added under ice cooling conditions, followed by stirring at room temperature for 1 hour. 2 ml of 5 N hydrochloric acid was added to the reaction mixture, followed by concentration under reduced pressure. The residue was adjusted to pH 7 by the addition of aqueous sodium carbonate and extracted 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. The desired fraction was collected and concentrated; the crystal obtained was collected by filtration to yield 0.488 g of the title compound.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. concentrationfollowed by concentration under reduced pressure
  3. additionThe residue was adjusted to pH 7 by the addition of aqueous sodium carbonate
  4. extractionextracted with ethyl acetate
  5. washthe extract was washed with saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted with ethyl acetate
  9. customThe desired fraction was collected
  10. concentrationconcentrated
  11. customthe crystal obtained
  12. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f552a08bc6cf490a8649a9b7a3dfd2f0
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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