2-Dimethylaminopyridine → N-(3,5-Dimethylisoxazol-4-ylsulphonyl)-6-[N-(5-bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxamide

Participants

Reaction Steps

6-[N-(5-Bromo-2-(2-methylprop-2-en-1-yloxy)benzyl)-N-ethylamino]pyridazine-3-carboxylic acid (example 2, compound 15) (187 mg, 0.46 mmol) was dissolved in dichloromethane (20 ml) and (1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDAC),(133 mg, 0.69 mmol), dimethylaminopyridine (DMAP) (113 mg, 0.92 mmol) and 3,5-dimethylisoxazol-4-ylsulfonamide (98 mg, 0.56 mmol) were added. The mixture was stirred at ambient temperature under argon for 72 hours, after which TLC (25% water/methanol) suggested the reaction was complete. The reaction mixture was loaded directly onto a MPLC column (silica) and the title compound obtained by elution 2.5% ethanol/dichloromethane followed by 0.5% acetic acid/2.5% ethanol/dichloromethane as a gum which was triturated with hexane to give the title product as a solid (98 mg, 38%).

Provenance & Evidence