3-(Tert-butoxy)benzoic acid → 3-tert-butoxy-N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]benzamide

To a solution of 3-tert-butoxybenzoic acid (64 mg, 0.330 mmol) in pyridine (3.0 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (125 mg, 0.330 mmol), and the mixture was stirred at room temperature for 10 min. N-[5-(5-Amino-2-methylphenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (102 mg, 0.30 mmol) was added to the obtained solution, and the mixture was stirred at 70° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate (100 mL)/tetrahydrofuran (10 mL), washed with 1% aqueous citric acid solution (100 mL), 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diisopropyl ether to give the title compound (88 mg, 57%) as a colorless powder.

1. stirringthe mixture was stirred at 70° C. for 4 hr
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionthe obtained residue was diluted with ethyl acetate (100 mL)/tetrahydrofuran (10 mL)
4. washwashed with 1% aqueous citric acid solution (100 mL), 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe insoluble material was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe obtained residue was triturated with diisopropyl ether

ORD-Eintrag

ord-fab59eb45ec2411d872efaa80734e2c1

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08344135B2