Acetylcysteamine → 6-(2-Acetylaminoethylthio)imidazo[1,2-b]pyridazine

Reaction equation

[C:1]([NH:4][CH2:5][CH2:6][SH:7])(=[O:3])[CH3:2].[H-].[Na+].Cl[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[N:16]=1>C(O)C>[C:1]([NH:4][CH2:5][CH2:6][S:7][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:17]=[CH:18][N:19]=2)[N:16]=1)(=[O:3])[CH3:2]

Participants

Procedure

To 30 ml of ethanol is added 1.79 g of N-acetylcysteamine and with ice-cooling and stirring, 720 mg of sodium hydride (oily, 60 wt.%) is added. Then, 1.54 g of 6-chloroimidazo[1,2-b]pyridazine is further added and the mixture is stirred at 50° C. for 4 hours. The solvent is distilled off under reduced pressure and the residue is diluted with a saturated aqueous solution of sodium hydrogen carbonate and extracted with chloroform. The extract is dried over magnesium sulfate and the solvent is distilled off under reduced pressure. The residue is subjected to silica gel (50 g) column chromatography and after the column is washed with ethyl acetate, elution is carried out with acetone. The eluate is concentrated under reduced pressure to give 1.83 g of 6-(2-acetylaminoethylthio)imidazo[1,2-b]pyridazine as colorless powders.