Trifluoroacetic acid → 3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-(piperidin-4-yl)ethyl)urea HCl salt

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Reaction Steps

To tert-butyl 4-(2-(3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)ethyl)piperidine-1-carboxylate (0.29 g, 0.4 mmol) dissolved in DCM (2 ml) was added TFA (0.5 ml, 7 mmol). The resulting mixture was stirred at room temperature for 2 hours. After this time the mixture was concentrated under reduced pressure and the residue triturated with diethyl ether. The pale yellow solid was filtered, washed with ether and dried under vacuum. This solid TFA salt was partitioned between DCM and saturated aqueous NaHCO3. The aqueous was re-extracted with DCM (×2). The combined organic extracts were dried over MgSO4 and concentrated up. The residue was taken up in dry DCM and HCl (2M in diethyl ether) was added. The cloudy solution was conc under reduced pressure and dried under high vac to give 3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-(piperidin-4-yl)ethyl)urea HCl salt 51 as a pale yellow solid.

Provenance & Evidence