2-Aminopropanol → 1-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxy-1-methylethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

A solution of ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.025 g, 0.049 mmol) in EtOH (1 mL) under nitrogen was treated with 2-amino-1-propanol (0.0041 mL, 0.051 mmol) for 10 min. (150° C. in a microwave vessel. An additional 0.001 mL of the amine was added to the reaction and it was further microwaved for 20 min.@150° C. The reaction was then cooled to ambient temperature and the resulting suspension was filtered, washed with EtOH and then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97 (d, J=6.59 Hz, 3 H), 3.25-3.31 (m, 2 H), 3.86-3.95 (m, 3 H), 4.11 (s, 2 H), 4.43-4.52 (m, 1 H), 4.57-4.65 (m, 1 H), 4.90 (t, J=5.31 Hz, 1 H), 7.10-7.16 (m, 2 H), 7.31-7.38 (m, 2 H), 7.80-7.85 (m, 4 H), 8.15-8.18 (m, 1 H), 8.52 (d, J=1.46 Hz, 1 H), 9.96 (d, J=7.87 Hz, 1 H), 17.25 (s, 1 H); ES+ MS: 545 (M+H+).

Provenance & Evidence