Acetic Acid → 2-(4-Chloro-phenyl)-5-{3-methoxy-4-[1-(tetrahydro-pyran-4-yl)-azetidin-3-yloxy]-phenyl}-5H-thiazolo[5,4-c]pyridin-4-one, hydrochloride salt

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Reaction Steps

Suspend 5-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one (50 mg, 0.11 mmol) in MeOH (5.68 mL). Add tetrahydro-4H-pyran-4-one (15.7 μL, 0.17 mmol) and acetic acid (9.8 μL, 0.17 mmol) and stir at room temperature for 10 min. Add sodium cyanoborohydride (7.1 mg, 0.11 mmol) and stir at room temperature for 6 h. Add dichloromethane to the reaction mixture to dissolve the solid material. Pour onto a 2 g SCX2 ion exchange column wet with MeOH and elute under gravity. Elute SCX cartridge with MeOH (approximately 3 volumes) under reduced pressure and discard. Elute SCX cartridge with 7N NH3 in MeOH:dichloromethane (1:1) (approximately 5 volumes) under reduced pressure and then concentrate in vacuo. Dissolve the resultant solid in dichloromethane (5 mL) and add 4 N HCl in dioxane solution (25 μL). Evaporate the solvent and suspend the solid in water. Freeze-dry to give (51 mg, 83%) of the title compound as a white solid. ES/MS m/z (35Cl) 524 [M+1]+.

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