Hydrazine → HCID 58914780, compound

Participants

Reaction Conditions

Reaction Steps

Hydrazine (1.3 eq) was added to a solution of 2-{3-[4-(2,4-dichlorophenyl)-3-(4-methyl-2-oxopiperazinyl)pyrrolyl]propyl}benzo[c]azoline-1,3-dione (8) in abs. EtOH and stirred at 75° C. for 2 hours. The reaction developed a white precipitate, which was filtered. The EtOH was concentrated under reduced pressure. The residue was taken up in CH2Cl2 and the precipitate was filtered again. The organic solution was evaporated to a foam. Assuming a quantitative yield, the residue was taken up in CH3CN and DMA (4:1). Hünig's Base (1.3 eq) was added to the mixture followed by 6-chloro-3-nitro-2-pyridylamine (10) (1.2 eq). The reaction was heated to 80° C. for 2 hours until completion was determined by LC/MS. The reaction was subsequently concentrated. The residue was dissolved in EtOAc, washed with water, brine, dried (Na2SO4), filtered, and concentrated to dryness to give 1-(1-{3-[(6-amino-5-nitro(2-pyridyl))amino]propyl}-4-(2,4-dichlorophenyl)pyrrol-3-yl)-4-methylpiperazin-2-one (11). The product (11) was purified by silica column chromatography, eluting with MeOH in CH2Cl2 (5:95, v/v). After collecting the purified fractions and concentrating, light yellow foam (LC/MS m/z 519.4 MH+, 42% yield) was attained in 95% purity.

Provenance & Evidence