Acetonitrile → HCID 68672745, compound

Participants

Reaction Conditions

Reaction Steps

1,2,4-triazole (3.73 g, 54 mmol) was suspended in dry acetonitrile (42 mL) and cooled to 0° C. in an ice bath. POCl3 (1.44 mL, 15.4 mmol) was added drop wise with stirring. TEA (10.73 mL, 77 mmol) was added slowly with vigorous stirring and the mixture was stirred at this temperature for an additional 30 min. A solution of Compound 19 (2.43 g, 3.85 mmol) in dry acetonitrile (14 mL) was added and the mixture stirred at 0° C. for 2 h and at room temperature for 1 hr. The solvents were removed under reduced pressure and the residue taken up in ethyl acetate. The ethyl acetate solution was washed twice with saturated sodium bicarbonate solution, once with brine and dried over anhydrous sodium sulfate. The solvents were removed under reduced pressure and the residue was taken up in dioxane (40 mL) and 30% ammonium hydroxide solution (20 mL) was added. The mixture was stirred in a sealed flask overnight at room temperature. The solvents were removed under reduced pressure and the residue purified by flash chromatography (10% methanol in dichloromethane) to give Compound 20, (2.0 g) in 75% yield.

Provenance & Evidence