Potassium Iodide → 5-Morpholin-4-yl-pentanoic acid {4-[3-(4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide

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Reaction Steps

To a solution of 5-bromo-pentanoic acid {4-[3-(4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide (intermediate JH140, prepared as described for tenovin 6) (80 mg, 0.16 mmol) in acetonitrile (4 mL) was added morpholine (0.4 mL) and potassium iodide (cat. amount). The reaction mixture was heated at reflux for 40 min, cooled to rt and concentrated in vacuo. The remaining residue was partitioned between 75% saturated aqueous sodium bicarbonate and CH2Cl2. The organic layer was dried with MgSO4 and concentrated in vacuo to give a crude beige solid. Purification by recrystallisation from EtOAc gave 5-morpholin-4-yl-pentanoic acid {4-[3-(4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide which was converted to the hydrochloride salt by vapour diffusion. A solution of the dimethylamine in 25% CDCl3/diethyl ether was exposed to hydrogen chloride to give 1 as a white precipitate which was collected by filtration.

Provenance & Evidence