Acetic Acid → HCID 89692879, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 ml round-bottom flask equipped with a magnetic stir bar, the iron powder (204.00 mg, 3.65 mmol) was suspended in clean, dry ethanol (8.00 ml, 137.01 mmol) at room temperature under an inert nitrogen atmosphere. To this was added the 7-nitro-2-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-6-(4-o-tolyl-piperazin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one 10c (71.80 mg, 0.15 mmol) dissolved in 1 ml of ethanol followed by the addition of acetic acid (2.00 ml, 34.94 mmol). The reaction mixture was warmed to 75° C. and was allowed to stir overnight. The reaction was cooled to room temperature and the mixture was filtered through Celite, washing with methanol. The collected solution was then concentrated under reduced pressure. The resultant ruby red oil was then diluted with 50 ml of ethyl acetate and the solution was neutralized with 30 ml of saturated NaHCO3 (aq) solution. The layers were then separated and the product was extracted from the aqueous using ethyl acetate (3×30 ml). The organic phases were combined, washed with brine (1×50 ml) and dried over Na2SO4. The solution was then decanted and the solvent was removed under reduced pressure. The product was then purified from the ruby red concentrate using silica gel column chromatography, eluting a gradient of 100% dichloromethane to 10% MeOH in dichloromethane. The product, 7-amino-2-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-6-(4-o-tolyl-piperazin-1-yl)-3,4-dihydro-2H-isoquinolin-1-one 10d (48.10 mg, 0.10 mmol), was isolated as an off-white solid and was carried forward without further purification. LCMS (m/e)=462 (M+H).

Provenance & Evidence