2-Methoxyaniline → HCID 178470157, compound

Participants

Reaction Steps

(±)-4-(4-Chlorophenyl)-6-ethoxycarbonyl-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (2.0 g) is dissolved in dimethylformamide (20 ml). 1-Hydroxybenzotriazole (HOBt, 0.81 g), N-dimethylaminopropyl-N'-ethylcarbodiimide hydrochloride (WSC, 1.10 g) and triethyl amine (0.77 ml) are added in order under ice-cooling, and the mixture is stirred. Ten minutes later, a solution of 2-methoxyaniline (0.65 g) dissolved in dimethylformamide (6 ml) is dropwise added to the reaction mixture, and the mixture is stirred at room temperature overnight. The reaction mixture is poured into water and extracted with toluene. The organic layer is washed with a 10% aqueous solution of hydrochloric acid, an aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate. After removing the solvent, the residue is recrystallized from ethanol to give 1.55 g of (±)-ethyl 4-(4-chlorophenyl)-6-(2-methoxyanilino)-carbonylmethyl-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4, 3-a][1,4]diazepine-6-carboxylate. 1/2 hydrate, melting point 136°-138° C.

Provenance & Evidence