C([O:9][C@H:10]1[C@:14]([F:16])([CH3:15])[C@H:13]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([NH2:27])=[N:21][C:22]=3Cl)[O:12][C@@H:11]1[CH2:28][O:29]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+].C[C:42](O)=[O:43]>CO>[NH2:27][C:20]1[N:19]=[C:18]2[C:23]([N:24]=[CH:25][N:17]2[C@@H:13]2[O:12][C@H:11]([CH2:28][OH:29])[C@@H:10]([OH:9])[C@:14]2([F:16])[CH3:15])=[C:22]([O:43][CH3:42])[N:21]=1To a suspension of 4 (500 mg, 0.951 mmol) in MeOH (10 ml) was added NaOMe in MeOH (25%, 0.90 ml). The mixture was heated to 50° C. for 3 h. Then, it was neutralized with AcOH. It was concentrated and EtOAC (30 ml) was added. The insoluble solid was filtered off The filtrate was concentrated and purified by flash column chromatography on silica gel using 0 to 15% MeOH in CH2Cl2 as eluents. Compound 7 (203 mg, 68.3%) was obtained as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.17 (s, 1H), 6.61 (s, 2H), 6.05 (d, J=17.6 Hz, 1H), 5.67 (d, J=7.2 Hz, 1H), 5.25 (t, J=4.8 Hz, 1H), 4.18 (dt, J=25.6, 8.0 Hz, 1H), 3.96 (s, 3H), 3.91 (dm, J=9.2 Hz, 1H), 3.85 (ddd, J=2.0, 5.2, 12.8 Hz, 1H), 3.69 (ddd, J=2.8, 3.2, 12.0 Hz, 1H), 1.06 (d, J=22.8 Hz, 3H); tR=0.52 (99.1%); LRMS (ESI) [M+H]+ calculated for C12H17FN5O4 314.3, found 314.2.
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