2-(Dimethylamino)acetyl chloride hydrochloride → N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-N2,N2-dimethylglycinamide

HRID 1663632Notes

Reaction equation

HRID 1663632 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1.Cl.[CH3:13][N:14]([CH2:16][C:17](Cl)=[O:18])[CH3:15]>CN1CCCC1=O.[OH-].[Na+]>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:17](=[O:18])[CH2:16][N:14]([CH3:15])[CH3:13])[N:10]=2)[N:7]=1

Participants

5

Reactant 2

HCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amine

Product 1

HCID 57708588N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-N2,N2-dimethylglycinamideYield 74%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 6-iodoimidazo[1,2-b]pyridazin-2-amine (1040 mg, 4.0 mmol) in N-methylpyrrolidone (5.0 mL) was added dimethylaminoacetyl chloride hydrochloride (948 mg, 6.0 mmol), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→70/30), and precipitated from diisopropyl ether to give the title compound (1019 mg, 74%) as a pale-yellow powder.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→70/30)
  4. customprecipitated from diisopropyl ether

Sources & evidence

ORD record
ord-c9a66128801a4212984dbe53ca55c0ef
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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