Acetic Acid → HCID 131729253, compound

Participants

Reaction Steps

Add cyclobutanone (0.4 mL, 5.4 mmol) to a solution of 5-(4-(azetidin-3-yloxy)phenyl)-2-(4-chlorophenyl)thiazolo[5,4-c]pyridin-4(5H)-one (0.44 g, 1.08 mmol) in methanol (54 mL) and acetic acid (0.31 mL, 5.4 mmol). Stir the mixture at room temperature for one hour, add sodium triacetoxyborohydride (1.4 g, 6.48 mmol) and continue stirring at room temperature overnight. Dilute the mixture with dichloromethane, then wash with saturated NaHCO3 solution and water. Dry the organic portion over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, using 0-10% MeOH/CH2Cl2 as eluent. Dissolve the solid with dichloromethane and add 1 M HCl/ether (1 eq). Stir the solution for 15 min. Concentrate the solid and filter with ether to give 0.31 g (58%) of the title compound. ES/MS m/z (35Cl) 464 [M+1]+.

Provenance & Evidence