Aniline → HCID 66778071, compound

Participants

Reaction Steps

2-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid obtained in Preparation Example 5-1 (25 mg) was dissolved in N,N-dimethylformamide (0.5 mL). Aniline (7.2 mg), 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (40.6 mg), 1-hydroxybenzotriazole (28.6 mg) and N,N-diisopropylethylamine (75.7 μL) were sequentially added and the mixture was stirred at room temperature for five hours. Ethyl acetate and water were added to the reaction solution, and the organic layer and the aqueous layer were separated. The aqueous layer was further extracted with ethyl acetate. The resulting organic layers were combined, sprayed with nitrogen gas and concentrated. The residue was purified by NH silica gel column chromatography to obtain the title compound (14.1 mg). The compound was further separated by CHIRALPAK™ IA (2 cm×25 cm; mobile phase:hexane:ethanol=50:50) to obtain the title compound with a retention time of 7.6 minutes (4.5 mg). The property values of the compound are as follows.

Provenance & Evidence