Ethanol → 3-imidazo[1,2-b]pyridazin-7-yl-N-methylbenzamide

HRID 1097320Notes

Reaction equation

HRID 1097320 reaction equation
[NH2:1][CH:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([NH:13][CH3:14])=[O:12])=[CH:3]1.C([O-])(O)=O.[Na+].[CH3:23][CH2:24]O>>[N:1]1[CH:23]=[CH:24][N:7]2[C:2]=1[CH:3]=[C:4]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([NH:13][CH3:14])=[O:12])[CH:5]=[N:6]2

Participants

4

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 594434953-(6-Amino-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide

Product 1

HCID 594435013-imidazo[1,2-b]pyridazin-7-yl-N-methylbenzamide

Procedure

3-(6-Amino-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide (1 eq, 1.07 mmol, 245 mg) is added to a solution of chloroacetic aldehyde (5 eq, 5.4 mmol, 0.69 ml) in EtOH (15 ml). NaHCO3 (2 eq, 2.15 mmol, 180 mg) is then added and the reaction mixture is heated at reflux for 17 h. The solvent is then removed in vacuo and the product is purified by flash column chromatography eluting with 9:1 DCM/MeOH to afford 3-imidazo-[1,2-b]-pyridazin-7-yl-N-methyl-benzamide as an orange solid; [M+H]+=253

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 17 h
  3. customThe solvent is then removed in vacuo
  4. customthe product is purified by flash column chromatography
  5. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-fa0f24d095c74567951526d3fda4b365
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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