Aniline → HCID 59378050, compound

Participants

Reaction Steps

To a stirred mixture of O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.56 g, 1.48 mmol) and aniline (0.13 g, 1.35 mmol) in dichloromethane (10 mL) was added over 5 min the solution of crude 2-(3-methyl[1,2,4]thiadiazol-5-yl)octanedioic acid 8-ethyl ester (2021039) and triethylamine in dichloromethane. The resultant reaction mixture was then stirred at room temperature overnight before being quenched with citric acid (5 g) in water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic fractions were dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (3:1 hexane/ethyl acetate followed by 1:1 hexane/ethyl acetate) to afford 7-(3-methyl[1,2,4]thiadiazol-5-yl)-7-phenylcarbamoyl heptanoic acid ethyl ester (2021040) (310 mg, 52% over two steps) as a yellow oil.

Provenance & Evidence