Triethylamine → N-(6-chloroimidazo-[1,2-b]pyridazine-2-carbonyl)glycine ethyl ester

HRID 1067592Notes

Reaction equation

HRID 1067592 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[N:7]=1.Cl.[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH2:20])[CH3:16].C(N(CC)CC)C>CN(C)C=O>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH:20][C:11]([C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][N:6]2[CH:8]=1)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27946376-Chloroimidazo[1,2-b]pyridazine-2-carboxylic acid

Product 1

HCID 22989255N-(6-chloroimidazo-[1,2-b]pyridazine-2-carbonyl)glycine ethyl esterYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.593 g of 6-chloroimidazo[1,2-b]pyridazine-2-carboxylic acid was suspended in 7.5 ml of N,N-dimethylformamide; 0.535 g of N,N′-carbonyldiimidazole and 0.46 g of glycine ethyl ester hydrochloride were added, followed by stirring at room temperature for 30 minutes. To this mixture, 0.457 ml of triethylamine was added, followed by further stirring for 1 hour. Ice water was added to the reaction mixture; the crystal precipitated was collected by filtration, washed with water and dried to yield 0.749 g of the title compound.

Workup

  1. stirringby further stirring for 1 hour
  2. customthe crystal precipitated
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-132f63a841af42e4826861326c370ef8
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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