Potassium Carbonate → HCID 72550657, compound

Participants

Reaction Steps

To a solution of methylhydroxylamine hydrochloride (23 mg, 0.28 mmol) in methanol (2 mL) was added potassium carbonate (44 mg, 0.32 mmol) followed by (E)-N-(2-(3-(trifluoromethyl)phenyl)-6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)cyanamide (50 mg, 0.16 mmol). The reaction mixture was stirred at room temperature for 1 hr. The mixture was concentrated in vacuo and the crude residue partitioned between dichloromethane and water. The product was extracted into dichloromethane (×3). The organic extracts were combined, dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified using preparative HPLC to give the title compound as yellow solid (34.2 mg, 58%). (regioisomeric mix with 2′-methyl-2-(3-(trifluoromethyl)phenyl)-6,7-dihydro-2′H, 5H-spiro[benzo[b]thiophene-4,3′-[1,2,4]oxadiazol]-5′-amine). 1H NMR δ (ppm)(DMSO-d6): 7.87-7.80 (2H, m), 7.64-7.58 (2H, m), 7.34 (1H, s), 6.12 (2H, s), 2.94 (3H, s), 2.80-2.60 (2H, m), 1.93-1.80 (3H, m), 1.80-1.69 (1H, m). HPLC (Method a) Rt 8.05 (min) m/z 368 (MH+).

Provenance & Evidence