HCID 54269484, compound → HCID 54424075, compound

Participants

Reaction Steps

To a stirred solution of 2-[2,4-dioxo-3-(phenyl-hydrazono)-5-pyrimidin-2-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepine-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (500 mg, 0.886 mmol) in acetic acid (12 mL) at ambient temperature was added zinc dust (530 mg) and the resulting mixture was stirred 1 h. The zinc was separated by filtration, the filtrate concentrated in vacuo, and the resultant oil partitioned between water (30 mL) and ethyl acetate (80 mL). The pH was adjusted to 8 with 6N sodium hydroxide and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×35 mL) and the organics combined, dried with magnesium sulfate, filtered and concentrated in vacuo to give a yellow foam. The crude product was purified via flash chromatography on silica gel (15 g) eluting with methylene chloride/methanol (19:1, 250 ml). Appropriate fractions were combined and concentrated to give the title compound (255 mg, 0.537 mmol) as a white glass:

Provenance & Evidence