Water → HCID 136011087, compound

Participants

Reaction Steps

To a solution of ethyl 5-{2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrol-5-yl}-1,3,4-thiadiazole-2-carboxylate (1.3 g) in tetrahydrofuran (20 mL) was slowly added lithium aluminum hydride (114 mg) in small portions. The mixture was stirred at room temperature for 1 hr, and water (0.15 mL), 15% aqueous sodium hydroxide solution (0.15 mL) and water (0.45 mL) were successively added to the reaction mixture under ice-cooling. The mixture was stirred for 1 hr, and the insoluble material was filtered off. The filtrate was concentrated and crystallized from diethyl ether to give N-{5-[5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl]-2-methyl-4H-thieno[3,2-b]pyrrol-3-yl}-N-methylthiophene-2-sulfonamide (370 mg, yield 31%) as brown crystals.

Provenance & Evidence