[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.CO.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1
As shown in Reaction Scheme 5, methyl 3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]biphenyl-4-carboxylate (0.64 g, 1.6 mmol) was suspended in THF (10 mL), MeOH (10 mL) and water (5 mL), and LiOH (0.39 g, 16.2 mmol) was added. The reaction mixture was heated at 50° C. until dissolution was achieved, and then the mixture was stirred for 3 days at rt. The reaction mixture was brought to pH 4 with 1N HCl and was extracted with EtOAc (3×25 mL). The combined organic phases were washed with water (2×50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. This yielded 0.518 g (84%) of the desired product as an off-white solid. LC/MS m/z 383.3 (MH+), retention time 3.83 min. 1H NMR (400 MHz, DMSO-d6) δ 7.18 (t, 1H), 7.59-8.00 (m, 8H), 8.70 (t, 1H), 10.50 (bs, 1H), 12.95 (bs, 1H).
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