Dimethylformamide → (+/-)-N-(3-pyridylmethyl)-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 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 (1.0 g) and benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (1.2 g) are added to dimethylformamide (20 ml), and the mixture is stirred. 3-(Aminomethyl)pyridine (0.30 g) and triethylamine (0.38 g) are added, and the mixture is stirred at room temperature for 6 hours. After the completion of the reaction, water (200 ml) is added and the mixture is extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is crystallized from ethyl acetate and isopropyl ether, and recrystallized from ethanol to give 200 mg of (±)-N-(3-pyridylmethyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide 1/2 1759 hydrate as white powdery crystals, melting point 180°-183° C.

Provenance & Evidence