Ethanol → 3-imidazo[1,2-b]pyridazin-7-yl-N-methylbenzamide
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]2Participants
4
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