[CH:1]([C:4]1[C:13]2[CH:14]=[CH:15][C:16]([C:18](O)=[O:19])=[CH:17][C:12]=2[C:11]2[C:10](=[O:21])[NH:9][CH:8]=[CH:7][C:6]=2[N:5]=1)([CH3:3])[CH3:2].C(N1C=CN=C1)([N:24]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[CH:1]([C:4]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([NH2:24])=[O:19])=[CH:17][C:12]=2[C:11]2[C:10](=[O:21])[NH:9][CH:8]=[CH:7][C:6]=2[N:5]=1)([CH3:3])[CH3:2]To a stirred suspension of 6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid (78 mg, 0.28 mmol) in DMF (1.0 mL) was added 1,1′-carbonylbis(1H-imidazole) (CDI, 68 mg, 0.42 mmol). The reaction mixture was stirred for 1 hour at room temperature. Ammonium hydroxide (0.19 mL, 1.3 mmol) was added, and the resulting mixture was stirred for 15 minutes. The reaction mixture was diluted with DMF and purified directly by preparative reverse phase HPLC, eluting with an acetonitrile/water (with 0.05% TFA modifier) gradient to afford 6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxamide. 1H NMR (500 MHz, DMSO-D6) δ 11.86 (s, 1H), 10.46 (s, 1H), 8.50 (d, 1H), 8.20 (s, 1H), 8.09 (d, 1H), 7.61 (s, 1H), 7.56 (t, 1H), 6.78 (d, 1H), 4.12 (septet, 1H), 1.37 (d, 6H). LRMS (ESI) calc'd for (C16H15N3O2) [M+H]+, 282.1; found 282.1.
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