Nitrogen → HCID 73214161, compound

Participants

Reaction Steps

A solution of (S)-benzyl (1-isopropoxy-3-((6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)propan-2-yl)carbamate (220 mg, 0.130 mmol) in MeOH (12 mL) was degassed with N2 for 5 min. Pd/C (68.9 mg, 0.065 mmol) was added and the mixture stirred under a balloon of H2 for 12 h. The reaction mixture was filtered through diatomaceous earth (Celite®), eluting with methanol and the filtrate was concentrated under reduced pressure. The residue was purified by reverse phase HPLC (10 MM ammonium acetate in water/AcCN) to afford (S)-8-(2-amino-3-isopropoxypropoxy)-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (90 mg, 0.108 mmol, 83% yield) as an off-white solid. LC/MS (ESI) m/e 342.2, [(M+H)+, calcd for C19H24N3O3, 342.2]; LC/MS retention time (method C): tR=1.50 min. HPLC retention time (method A): tR=7.20 min; HPLC retention time (method B): tR=8.00 min. 1H NMR (400 MHz, MeOD) δ ppm 9.54 (s, 1H), 8.23 (d, J=4.4 Hz, 1H), 8.52 (d, J=8.8 Hz, 1H), 8.44 (d, J=6.0 Hz, 1H), 7.20 (s, 1H), 7.18 (d, J=6.0 Hz, 1H), 4.52 (dd, J=10.4, 3.6 Hz, 1H), 4.43 (dd, J=10.4, 6.8 Hz, 1H), 3.88-3.75 (m, 7H), 1.26 (d, J=6.4 Hz, 3H), 1.25 (d, J=6.4 Hz, 3H).

Provenance & Evidence