Cl.[CH3:2][O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH2:22])=[N:18][CH:19]=1.C(N(C(C)C)CC)(C)C.[O:32]=[C:33]1[CH2:38][S:37][C:36]2[CH:39]=[CH:40][C:41]([C:43](O)=[O:44])=[N:42][C:35]=2[NH:34]1.O.OC1C2N=NNC=2C=CC=1.C(Cl)CCl>CN(C=O)C>[CH3:2][O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][C:43]([C:41]2[CH:40]=[CH:39][C:36]3[S:37][CH2:38][C:33](=[O:32])[NH:34][C:35]=3[N:42]=2)=[O:44])=[N:18][CH:19]=1To a stirred solution of (2-{5-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-pyridinyl}ethyl)amine hydrochloride salt (1.08 mmole) in DMF (25 mL) at RT was added diisopropylethylamine (0.75 mL, 4.32 mmole), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (0.23 g, 1.08 mmole), hydroxybenzotriazole hydrate (0.16 g, 1.19 mmole) and EDC (0.23 g, 1.19 mmole). After 18 h, the reaction contents were concentrated and dried under high vacuum. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.40 g, 79%) as light yellow solid: 1H NMR (400 MHz, CD3OD) δ 9.55 (m, 1H), 9.19 (m, 1H), 9.09 (d, J=8.3 Hz, 1H), 8.53 (d, J=9.2 Hz, 1H), 8.42 (m, 1H), 8.23 (d, J=7.7 Hz, 1H), 7.88 (d, J=8.3 Hz, 1H), 7.61 (m, 2H), 4.5 (s, 3H), 4.02 (m, 2H), 3.62 (m, 2H), 3.54 (m, 2H). LC-MS (ES) m/e 473 (M+H)+.
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