HCID 91325177, compound → N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]propanamide
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:29])=[CH:10][C:9]=1[F:30])(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[C:9]([F:30])=[CH:10][C:11]([Cl:29])=[C:12]([CH:13]=1)[O:14][C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[N:23][C:18]2=[CH:17][CH:16]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of tert-butyl(4-chloro-2-fluoro-5-{[2-(propanoylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}phenyl)carbamate (1.26 g, 2.70 mmol) and trifluoroacetic acid (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with aqueous sodium hydrogen carbonate solution (30 mL×2) and saturated brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=67/33→0/100) to give the title compound (787 mg, 79%) as white crystals.