Methanol → N-[5-(3-amino-4-chlorophenoxy) [1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide

Participants

Reaction Steps

Sodium borohydride (5.63 g, 149 mmol) was suspended in ethanol (100 mL), and methanol (66 mL) was gradually added. While cooling in a water bath, to the obtained reaction mixture was added N-(5-{4-chloro-3-[(trifluoroacetyl)amino]phenoxy}[1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide (3.4 g, 7.44 mmol) powder by small portions, and thereafter the mixture was stirred at room temperature, for 1 hr. The reaction mixture was diluted with ethyl acetate (150 mL), and partitioned with water (200 ml). The organic layer was concentrated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), and washed with saturated brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0), and triturated with diisopropyl ether to give the title compound (2.00 g, 75%) as a colorless powder.

Provenance & Evidence