3-(4-Tert-butylphenyl)-5-(chloromethyl)-1,2,4-oxadiazole → (R)-1-{4-[3-(4-tert-Butyl-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-piperazin-1-yl}-3-(2-methyl-benzothiazol-5-yloxy)-propan-2-ol

Participants

Reaction Steps

A solution of (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol, a compound of formula (6) (75 mg, 0.14 mmol), and 3-(4-tert-butylphenyl)-5-chloromethyl-1,2,4-oxadiazole (40 mg, 0.16 mmol) in 10% trimethylamine/ethanol, was heated to 73° C. and allowed to stir overnight. The solvent was evaporated under reduced pressure, and the resulting residue chromatographed by preparative thin layer chromatography (PTLC) (3% methanol/methylene chloride). The resulting oil was diluted with methylene chloride and placed on the high Vac. overnight, to yield (2R)-3-[4-({3-[4-(tert-butyl)phenyl](1,2,4-oxadiazol-5-yl)}methyl)piperazinyl]-1-(2-methylbenzothiazol-5-yloxy)propan-2-ol as a white solid.

Provenance & Evidence