3-(Trifluoromethyl)benzeneacetic acid → HCID 46219899, compound

Participants

Reaction Conditions

Reaction Steps

N-[5-(3-Amino-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (150 mg, 0.44 mmol) produced in Example 16(vi) was dissolved in N,N-dimethylacetamide (3.0 mL)/pyridine (9.0 mL), [3-(trifluoromethyl)phenyl]acetic acid (110 mg, 0.52 mmol) and 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (330 mg, 0.65 mmol) were added, and the mixture was stirred at 90° C. for 2 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (27 mL), and washed successively with water (27 mL) and saturated brine (27 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/hexane=50/50→100/0), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/heptane to give the title compound (78 mg, 34%) as a colorless powder.

Provenance & Evidence