[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH:29]([CH3:31])[CH3:30])=[O:24])[C:5]1=[O:32].C(N(C(C)C)CC)(C)C.Cl[C:43]([O:45][CH3:46])=[O:44]>CN(C=O)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:11]2[CH:12]=[C:13]3[C:8]([C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH:29]([CH3:30])[CH3:31])=[O:24])[C:5](=[O:32])[N:4]3[CH2:3][CH2:2][NH:1][C:43](=[O:44])[O:45][CH3:46])=[N:9][CH:10]=2)=[CH:20][CH:19]=1A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.020 g, 0.045 mmol) and diisopropyl ethylamine (0.04 mL, 0.23 mmol) in DMF (5 mL) under nitrogen was treated with methyl chloroformate (0.0036 mL, 0.047 mmol) at ambient temperature. The reaction was concentrated in vacuo and the resulting residue was treated with 1N NaHSO4. The resulting suspension was filtered, washed with EtOH and Et2O, and dried in vacuo to provide the title compound as an beige solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.12 (d, J=6.18 Hz, 6 H), 3.22-3.31 (m, 2 H), 3.45 (s, 3 H), 3.49-3.56 (m, 4 H), 3.61 (dt, J=12.07, 6.04 Hz, 1 H), 4.14 (s, 2 H), 4.29 (t, J=6.32 Hz, 2 H), 7.11-7.19 (m, 2 H), 7.26 (t, J=5.62 Hz, 1 H), 7.39 (dd, J=8.56, 5.48 Hz, 2 H), 8.12 (s, 1 H), 8.53 (s, 1 H), 10.38 (t, J=5.48 Hz, 1 H), 17.12 (s, 1 H); ES+ MS: 501 (M+H+).
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