[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.[ClH:15].Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[ClH:15].[ClH:15].[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([O:14][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1
A vial was charged with 2-(4-methylthiazol-2-ylamino)pyridin-3-ol (75 mg, 0.362 mmol), 2-(bromomethyl)pyridine hydrochloride (75.4 mg, 0.362 mmol), potassium carbonate (175 mg, 1.27 mmol), and DMF (3 mL), and the reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured into water and extracted with ether. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated, and purified over silica gel (80% EtOAc in hexanes). The residue was dissolved in 1:1 CH2Cl2:MeOH, and 2M HCl in ether was added. The solution was then concentrated to afford N-(4-methylthiazol-2-yl)-3-(pyridin-2-ylmethoxy)pyridin-2-amine dihydrochloride (96 mg, 71.4% yield) as a tan solid. 1H NMR (d6-DMSO) δ 8.77 (d, 1H), 8.19 (t, 1H), 8.07 (d, 1H), 8.04 (d, 1H), 7.67 (m, 2H), 7.16 (dd, 1H), 6.87 (s, 1H), 5.53 (s, 2H), 2.33 (s, 3H). Mass spectrum (apci) m/z=299 (M+H-2HCl).
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