Water → N-(6-chloro[1,2,4]triazolo[1,5-b]pyridazine-2-carbonyl)glycine ethyl ester

HRID 1067599Notes

Reaction equation

HRID 1067599 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[N:7]=1.C(N(C(C)C)C(C)C)C.Cl.[CH2:24]([O:26][C:27](=[O:30])[CH2:28][NH2:29])[CH3:25].O>CN(C)C=O>[CH2:24]([O:26][C:27](=[O:30])[CH2:28][NH:29][C:11]([C:9]1[N:10]=[C:5]2[N:6]([N:7]=[C:2]([Cl:1])[CH:3]=[CH:4]2)[N:8]=1)=[O:13])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 229892926-Chloro-[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylic acid

Product 1

HCID 22989303N-(6-chloro[1,2,4]triazolo[1,5-b]pyridazine-2-carbonyl)glycine ethyl esterYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.86 g of 6-chloro[1,2,4]triazolo[1,5-b]pyridazine-2-carboxylic acid and 2.72 ml of N-ethyldiisopropylamine were suspended in 30 ml of N,N-dimethylformamide; 2.63 g of N,N′-carbonyldiimidazole was added, followed by stirring at room temperature for 1 hour. To the reaction mixture, 2.21 g of glycine ethyl ester hydrochloride was added, followed by stirring at room temperature for 5 hours. Water was added; the crystal precipitated was collected by filtration, washed with water and ether and dried to yield 2.93 g of the title compound.

Workup

  1. stirringby stirring at room temperature for 5 hours
  2. customthe crystal precipitated
  3. filtrationwas collected by filtration
  4. washwashed with water and ether
  5. customdried

Sources & evidence

ORD record
ord-38e763a7e5274c8c9846c1713cfa7b29
Source dataset
uspto-grants-2001_06
Patent number
US06248740B1

Reaction notes

Loading…