Methanol → 4-Methoxy-N,2,6-trimethyl-N-[(5-{[4-(3-pyrrolidin-1-ylpropyl)piperazin-1-yl]carbonyl}-1,3,4-oxadiazol-2-yl)methyl]benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

1-(3-Pyrrolidin-1-ylpropyl)piperazine (128 mg, 1.65 mmol) was dissolved in THF (5 mL) and the resulting solution was cooled to −40° C. prior to the addition of trimethylaluminium (2 M in toluene, 0.59 mL). The reaction was stirred for 15 min at −40° C. and a solution of methyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (200 mg, 0.54 mmol) in THF (5 mL) was added dropwise. The reaction was stirred at ambient temperature for 18 h and MeOH (5 mL) was added. The solvents were removed in vacuo and the resulting residue was purified by FCC, eluting with 0-2% MeOH in DCM to afford the title compound as a pale yellow semi solid.

Provenance & Evidence