Acetic Acid → HCID 25160190, compound

Participants

Reaction Steps

To a suspension of (±)-5-cyclopropyl-7-(1-((4-(4-fluorophenyl)piperidin-4-yl)methoxy)ethyl)-1H-indazole (21.8 mg, 0.055 mmol) and sodium cyanoborohydride (17.4 mg, 0.277 mmol) in acetonitrile (1 mL) at 0° C. was added formalin (0.041 mL). The reaction was treated with 1 drop of acetic acid. After 5 min, a second drop of acetic acid was added. The ice bath was removed and stirring continued for another hour. The reaction was diluted with diethyl ether and washed with 1 M sodium hydroxide. The ethereal was concentrated and loaded onto a strong cation exchange cartridge in methanol. The cartridge was flushed with several volumes of methanol which were discarded. The product was eluted with 2 M ammonia in methanol and concentrated. It was then purified by preparative HPLC to give 7.8 mg (55.7%). LC/MS (HPLC method 3): tR=1.742 min, 393.07(MH)+.

Provenance & Evidence