Ethanolamine → HCID 69480952, compound
Reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33](OCC)=[O:34])[C:15]1=[O:38].[CH2:39]([CH2:41][NH2:42])[OH:40]>CCO>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:42][CH2:41][CH2:39][OH:40])=[O:34])[C:15]1=[O:38]Participants
4
Procedure
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 (0.035 g, 0.068 mmol) in EtOH (3 mL) under nitrogen was treated with Ethanolamine (8 mg, 0.13 mmol) for 2 h@150° C. in a microwave vessel. The reaction was then cooled to ambient temperature and the resulting suspension was filtered, washed with EtOH and Et2O and thoroughly dried under high vacuum to provide the title compound as an orange solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 3.4 (m, 5 H), 3.9 (t, J=6.0 Hz, 2 H), 4.1 (s, 2 H), 4.5 (t, J=5.8 Hz, 2 H), 4.8 (t, J=5.0 Hz, 1 H), 7.1 (ddd, J=9.0, 6.7, 2.2 Hz, 2 H), 7.3 (m, 2 H), 7.8 (m, 4 H), 8.1 (d, J=1.1 Hz, 1 H), 8.5 (d, J=1.3 Hz, 1 H), 10.0 (s, 1 H); ES+ MS: 531 (M+H+).