Sodium Bisulfate → HCID 69480377, compound

Participants

Reaction Steps

A mixture of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1-[2-(2-oxo-1-piperidinyl)ethyl]-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.064 mmol) and (2R)-2-amino-4-methyl-1-pentanol (75 μL, 0.64 mmol) was heated in EtOH (3 mL) at 175° C. for 45 min. in a microwave. The reaction mixture was cooled to rt and let stand overnight. Added 1N NaHSO4 (2 mL) filtered the resulting suspension, washed with EtOH:water 1:1, and Et2O then concentrated the filtrate in vacuo. Dissolved the residue in CH2Cl2, washed with 0.5N NaHSO4, water, and brine then dried the organics over Na2SO4, filtered and concentrated in vacuo. Triturated the residue with Et2O, filtered and dried in vacuo to provide the product as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.91 (d, J=6.53 Hz, 6 H), 1.40-1.50 (m, 2 H), 1.53-1.67 (m, 6 H), 1.99-2.11 (m, 2 H), 3.18-3.29 (m, 2 H), 3.35-3.50 (m, 4 H), 3.53-3.59 (m, 1 H), 4.09 (dd, J=4.32, 3.26 Hz, 1 H), 4.17 (s, 2 H), 4.93 (t, J=5.16 Hz, 1 H), 7.10-7.18 (m, 2 H), 7.37-7.44 (m, 2 H), 8.21 (d, J=1.47 Hz, 1 H), 8.56 (d, J=1.69 Hz, 1 H), 10.31 (d, J=9.06 Hz, 1 H), 17.27 (s, 1 H); ES+ MS: 539 (M+H+).

Provenance & Evidence