Ammonium Chloride → tert-butyl 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetate

Participants

Reaction Steps

To a solution of 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (200 mg, 0.62 mmol) in THF was added LiHMDS (0.9 mL, 0.9 mmol) at −78° C. The mixture was stirred at the same temperature for 1 h, and then tert-butyl 2-bromoacetate (180 mg, 0.92 mmol) was added, the mixture was warmed to room temperature and stirred overnight. NH4Cl aqueous (15 mL) was added, and then extracted with DCM (3×10 mL3). The combined organic layers were dried over Na2SO4, and the solvent was removed in vacuum. The residue was purified by column chromatography (silica-gel, DCM:MeOH=20:1) to give tert-butyl 2-(6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-4-yl)acetate as a yellow solid (140 mg, 51.4%). LRMS (M+H)+: 324 m/z. 1H NMR (300 MHz, CD3OD): δ 1.46 (s, 9H), 2.72 (s, 3H), 3.08-3.15 (m, 1H), 3.31-3.39 (m, 1H), 4.10-4.15 (m, 1H), 7.15-7.23 (m, 3H), 7.40-7.43 (m, 2H), 7.50-7.54 (m, 2H), 7.74-7.79 (m, 1H).

Provenance & Evidence