Aniline → HCID 19704929, compound

Participants

Reaction Steps

(±)-4-(4-(4-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)butyric acid (0.50 g) and 1-hydroxybenzotriazole (0.17 g) are added to dry dimethylformamide (20 ml) and the mixture is stirred under ice-cooling. Thereto is added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.25 g), and then triethylamine (0.24 g) and aniline (0.11 g) are added. The mixture is stirred at room temperature for 4 days. After the completion of the reaction, water (100 ml) is added and the mixture is extracted with ethyl acetate. The organic layer is washed with 6N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (ethyl acetate:methanol=10:l) and crystallized from ethyl acetate and isopropyl ether to give 0.29 g of (±)-N-phenyl-4-(4-(4-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo-[4,3-a][1,4]diazepin-6-yl)butaneamide as white powdery crystals, melting point 238°-240° C.

Provenance & Evidence