Triethylamine → HCID 58951395, compound

Participants

Reaction Steps

Add methanesulfonyl chloride (0.135 g, 0.935 mmol) to a cool (0° C.) solution of 2-[2-(4′-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethanol (0.257 g, 0.719 mmol) and triethylamine (0.182 g, 1.80 mmol) in dichloromethane (5 mL). Warm to room temperature and stir for 1 hour. Remove the solvents, transfer the residue to a sealed tube, add tetrahydrofuran (5 mL) and N-methyl-isopropylamine (0.526 g, 7.19 mmol), and heat at 60° C. overnight. Add dichloromethane and wash the crude organic material with saturated sodium chloride solution. Dry the organic layer over Na2SO4, filter, and concentrate. Purify on silica gel eluting with 5% ammoniated methanol in dichloromethane to give isopropyl-{2-[2-(4′-methanesulfonyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethyl}-methyl-amine (0.056 g, 18%): mass spectrum (m/e): 413 (M+1). Treat the recovered material (0.056 g, 0.131 mmol) with 1N HCl (144 μL, 0.144 mmol) in ether, concentrate, and lyophilize to give the title compound (12.8 mg): MS (m/e): 413 (M+1).

Provenance & Evidence