Benzoic Acid → HCID 178526364, compound

Participants

Reaction Steps

Benzoic acid (4.3 mg, 0.035 mmol) and 3-[4-(aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (10 mg, 0.032 mmol) was dissolved in ACN (0.2 mL) and DCM (0.2 mL). To the mixture was added DMAP (2.4 mg, 0.02 mmol) and DIPEA(17 μL, 0.096 mmol). After the mixture became a clear solution, bromotris(pyrrolydino)phosphonium hexa-fluorophosphate (16 mg, 0.035 mmol) was added, followed by additional DIPEA(17 μL, 0.0962 mmol). The reaction mixture was stirred at rt for 6 hrs. LCMS indicated 70% ratio of product to starting amine. The reaction was then diluted with MeOH and crude residue was purified by preparative LCMS. The intermediate was stripped to dryness, redissolved in EtOH (1 mL) and 1 M of sodium hydroxide in water (0.06 mL). The reaction was stirred for 1 hr at rt. The reaction was quenched with acetic acid and then diluted with MeOH and crude residue was purified by preparative LCMS to afford the desired product (1.1 mg). MF=C17H13ClFN5O3; LCMS calculated for C17H14ClFN5O3(M+H)+: m/z=390.077.

Provenance & Evidence