Diisopropylethylamine → 4-Methoxy-2,6-dimethyl-N-{5-[4-(1-methyl-piperidin-4-ylmethyl)-piperazine-1-carbonyl]-1,3,4-oxadiazol-2-ylmethyl}-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

4-methoxy-2,6-dimethylbenzenesulfonyl chloride (118 mg, 0.5 mmol) was added to a suspension of (5-Amino methyl-1,3,4-oxadiazol-2-yl)-[4-(1-methyl-piperidin-4-ylmethyl)-piperazin-1-yl]-methanone trihydrochloride (200 mg, 0.43 mmol) in DCM, under N2 and the mixture was cooled to −30° C. DIPEA (376 μL, 2.15 mmol) was added over about 3 min and the resultant pink solution was stirred at −30° C. for 30 min and then at ambient temperature for 16 h. The mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM (×2). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to a brown gum which was purified using FCC, eluting with 5% NH3 (2.0 M in MeOH) in DCM, to give the title compound as a clear gum.

Provenance & Evidence