1-Hydroxybenzotriazole → HCID 19864522, compound

Participants

Reaction Steps

To an ice cold mixture of 3-(4-fluorophenyl)-3-oxoproprionic acid (prepared by standard saponification of the commercially available ester) (0.69 g), 1-hydroxybenzotriazole (0.56 g), and 4-(2-methylimidazo[4,5-c]pyrid-1-yl)butylamine (see Preparation 24) (0.71 g) in methylene chloride (20 cm3) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.8 g) over 5 minutes. The mixture was stirred at 0° for 1 hour and then at room temperature for 30 minutes, poured into 5% sodium bicarbonate solution (50 ml) and extracted with methylene chloride (3×50 ml). The combined extracts were dried over Na2SO4, filtered and evaporated under vacuum. The residue was chromatographed on silica eluting with a methylene chloride/methanol mixture and the fractions containing the product were evaporated to give the title compound (0.82 g, 64%), which was used directly.

Provenance & Evidence