4-Aminobenzonitrile → HCID 178462384, compound

Participants

Reaction Steps

Trimethylaluminium (0.67 ml, 1.07M n-hexane solution, 0.72 mmol) was added dropwise to a solution of commercially available 4-aminobenzonitrile (85 mg, 0.72 mmol) in anhydrous toluene (4 ml) at room temperature with stirring under a nitrogen atmosphere. After stirring the mixture at room temperature for 10 minutes, a solution of methyl 6-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]-2-naphthalenecarboxylate (100 mg, 0.18 mmol) in anhydrous toluene (3 ml) was added dropwise to the resulting mixture. This mixture was stirred at 80C for 2.5 hours. At the end of this time to the reaction mixture were added sequentially water and 0.5N aqueous potassium sodium (+)-tartrate solution at room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was chromatographed on a silica gel column using ethyl acetate-hexane (3:1) as the eluant to afford the title compound (99 mg, yield 85%) as a colorless oil which was recrystallized from ethyl acetate-hexane to give white powdery crystals.

Provenance & Evidence