Oxalyl chloride → HCID 59507028, compound

Participants

Reaction Steps

2-Chloro-3-(1-cyano-1-methylethyl)benzoic acid (71.6 mg, 0.320 mmol) produced in Example C61(v) was dissolved in tetrahydrofuran (2 mL)/N,N-dimethylformamide (40 μL), oxalyl chloride (36 μL, 0.420 mmol) was added, and the mixture was stirred at room temperature for 45 min. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylacetamide (2 mL). N-[5-(5-Amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (79.8 mg, 0.211 mmol) was added, and the mixture was stirred at room temperature for 15 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution (5 mL), and the mixture was extracted with ethyl acetate (5 mL×4). The organic layer was washed successively with water (5 mL) and saturated brine (5 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→10/90), and crystallized from diisopropyl ether/ethyl acetate to give the title compound (63.4 mg, 51%) as white crystals.

Provenance & Evidence