4-Aminopyridine → (+/-)-N-(4-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo-[4,3-a][1,4]diazepine-6-acetamide

Participants

Reaction Conditions

Reaction Steps

(±)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (1.7 g) and triethylamine (0.65 ml) are added to a mixed solvent of dimethylformamide (20 ml) and tetrahydrofuran (10 ml). The mixture is cooled to -5° C. and pivaloyl chloride (0.57 ml) is dropwise added at said temperature. Ten minutes later, a solution of 4-aminopyridine (0.43 g) in dimethylformamide (2 ml) and tetrahydrofuran (2 ml) is dropwise added at said temperature, and the mixture is stirred at room temperature for 2 hours. Water is added to the reaction mixture, and the mixture is extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled away and the residue is recrystallized from isopropyl alcohol/isopropyl ether to give 1.29 g of (±)-N-(4-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo-[4,3-a][1,4]diazepine-6-acetamide, melting point 237°-239° C.

Provenance & Evidence