Sodium Hydroxide → 2-(4-Chloro-phenyl)-5-{4-[1-(2-hydroxy-ethyl)-azetidin-3-yloxy]-3-methoxy-phenyl}-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one, hydrochloride salt

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Reaction Steps

Dissolve 5-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (500 mg, 1.13 mmol) and 2,5-dihydroxy-1,4-dioxane (68 mg, 1.13 mmol) in dry 1,2-dichloroethane (6.66 mL). Add sodium triacetoxyborohydride (500 mg, 2.26 mmol) and stir overnight at room temperature. Add 1 N NaOH solution to the reaction mixture and extract with CH2Cl2 (2×25 mL). Combine the organic portions and wash with water (2×25 mL). Dry the organic layer with Na2SO4, filter, and concentrate in vacuo. Purify on HPLC, 4.6×75 mm XBridge® C18, Eluent: Reverse phase gradient 5-95% MeOH/water 0.1% TFA in 10 min, 2 mL/min. Re-dissolve the acquired material in CHCl3 and add 1 N HCl/Et2O solution (160 μL), followed by concentration in vacuo to give 65 mg (13%) of the title compound. ES/MS m/z (35Cl) 486.0 [M+1]+.

Provenance & Evidence