Hydrochloric Acid → HCID 135928045, compound

Participants

Reaction Conditions

Reaction Steps

152 mg crude N-Hydroxy-5-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-thiophene-2-carboxamidine were dissolved in 10 ml dichloromethane. 1.0 ml triethylamine and 43 ml phenylchloroformate were added at 0° C. and the mixture stirred at 0° C. for thirty minutes. The mixture was diluted by the addition of 10 ml acetonitrile and 97 μl 1,8-diazabicyclo[5.4.0]undec-7-ene were added. The mixture was stirred at 0° C. for 15 minutes. Then the mixture was poured on 100 ml 1M HCl and extracted five times with portions of 50 ml dichloromethane. The combined organic extracts were washed with 100 ml saturated NaHCO3 solution. The organic layer was then dried over MgSO4. The solvent was removed in vacuo. The resulting crude material was purified by chromatography on silica gel to obtain 125 mg 3-{5-[5-(4-Trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-thiophen-2-yl}-4H-[1,2,4]oxadiazol-5-one. C21H14F3N3O4S2 (493.49), MS (ESI−): 492.2 (M−H+).

Provenance & Evidence