[Cl:1][CH2:2][C:3](=O)[CH3:4].[CH2:6]([O:13][C:14]1[C:15]([NH:21][C:22]([NH2:24])=[S:23])=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.C(O)C>O>[ClH:1].[CH2:6]([O:13][C:14]1[C:15]([NH:21][C:22]2[S:23][CH:2]=[C:3]([CH3:4])[N:24]=2)=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1A 1 L round-bottomed flask was charged with 1-chloropropan-2-one (4.833 g, 52.24 mmol), 1-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (12.62 g, 37.31 mmol), triethylamine (8.841 mL, 63.43 mmol), and ethanol (30 mL). The reaction mixture was heated to reflux overnight, then poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated to provide 3-(benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine hydrochloride (11.5 g, 81.9% yield) as a white powder. 1H NMR (d6-DMSO) 8.05 (d, 1H), 7.77 (m, 1H), 7.59 (m, 2H), 7.43 (m, 2H), 7.37 (m, 1H), 6.79 (s, 1H), 5.33 (s, 2H), 2.29 (s, 3H). Mass spectrum (apci) m/z=378.0 (M+H-HCl). Analysis calculated for C16H15BrClN3OS: C, 46.56; H, 3.66; N, 10.18. found: C, 46.56; H, 3.77; N, 10.02.
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