Triethylamine → HCID 178493416, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 300 mg of 4-[4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-benzonitrile in 1.8 mL of tetrahydrofuran and 2 mL of methanol was added 387 mg of hydroxylamine hydrochloride followed by 0.62 mL of triethylamine. The resulting mixture was heated to 150° C. under microwave irradiation for 10 minutes. After allowing it to cool down to room temperature, the mixture was concentrated under reduced pressure and dichloromethane/water were added to the residue. The organic layer was separated and the aqueous layer extracted three times with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 50/ethyl acetate 50) to give 162 mg of 4-[4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-N-hydroxy-2-methoxy-benzamidine.

Provenance & Evidence