Triethylamine → N-(6-Chloroimidazo[1,2-b]pyridazine-2-carbonyl) beta-Alanine Ethyl Ester

HRID 1067601Notes

Reaction equation

HRID 1067601 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:22])[CH2:19][CH2:20][NH2:21])[CH3:16].C(N(CC)CC)C>CN(C)C=O>[CH2:15]([O:17][C:18](=[O:22])[CH2:19][CH2:20][NH:21][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 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27946376-Chloroimidazo[1,2-b]pyridazine-2-carboxylic acid

Product 1

HCID 22989218N-(6-Chloroimidazo[1,2-b]pyridazine-2-carbonyl) beta-Alanine Ethyl EsterYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.98 g of 6-chloroimidazo[1,2-b]pyridazine-2-carboxylic acid was suspended in 25 ml of N,N-dimethylformamide; 1.78 g of N,N′-dicarbonylimidazole was added, followed by stirring at room temperature for 1 hour. To this mixture, 1.69 g of β-alanine ethyl ester hydrochloride and 1.53 ml of triethylamine were added, followed by further stirring for 3 hours. Ice water was added to the reaction mixture; the crystal precipitated was collected by filtration, washed with water and dried to yield 2.57 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-296bf4575d704f128b5a9003a614d31a
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

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