Thioglycolic Acid → 1,3,3,5-Tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Participants

Reaction Steps

Lithium hydroxide (0.36 g, 15 mmol) and thioglycolic acid (0.48 ml, 6.9 mmol) were added to a DMF solution (20 ml) of 2-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1,3,3,5-tetramethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide (2.05 g, 3.4 mmol), and stirred at room temperature for 3 days. The reaction mixture was added to ice water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→dichloromethane:methanol=10:1→4:1). The purified product was concentrated under reduced pressure to thereby obtain 1.13 g (yield: 81%) of 1,3,3,5-tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a yellow oil.

Provenance & Evidence