Acetic Acid → HCID 178457985, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(2-(((benzyloxy)carbonyl)amino)-2-methylpropanoyl)-5-oxo-1,2,3,4,5,10-hexahydrobenzo[b][1,7]naphthyridine-6-carboxylate (0.11 g) and hydrazine hydrate (1.0 mL) in DMA (1.5 mL) was heated at 130° C. for 1.5 h, acetic acid (2.0 mL) was added and the mixture was stirred at 130° C. for another 12 hours. The reaction mixture was cooled to room temperature, then water (15 mL) and EtOAc (50 mL) were added. The organic phase was separated and then washed with aqueous NaHCO3 (2×10 ml) and brine (20 ml), dried over Na2SO4, filtered, the organic phase was concentrated in vacuum to give the crude product, which was purified by Pre-HPLC to afford benzyl (2-methyl-1-oxo-1-(3-oxo-10,11-dihydro-2H-phthalazino[8,1-bc][1,7]naphthyridin-9(3H,7H,8H)-yl)propan-2-yl)carbamate (46 mg, 42%) as a yellow solid. 1H NMR (DMSO-d6) δ 11.8 (s, 1H), 10.6 (s, 1H), 8.4 (s, 1H), 7.65 (t, 1H, J=7.8 Hz), 7.49 (d, 1H, J=7.8 Hz), 7.25-7.35 (m, 6H), 4.90-4.91 (m, 2H), 4.34-4.40 (m, 2H), 3.83-3.89 (m 2H), 2.32-2.34 (m, 2H), and 1.40 (s, 6H). MS (ESI) m/e [M+1]+460.0.

Provenance & Evidence