Sodium Carbonate → Butyl [3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]carbamate

To a solution of tert-butyl {3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}carbamate (800 mg, 2.14 mmol) in pyridine (10 mL) was added cyclopropanecarbonyl chloride (390 μL, 4.29 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with methanol (20 mL), anhydrous sodium carbonate (1.0 g, 9.43 mmol) was added, and the mixture was stirred at room temperature for 6 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (100 mL)/tetrahydrofuran (10 mL), washed with 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 ethyl acetate and diisopropyl ether to give the title compound (880 mg, 93%) as a pale-yellow powder.

1. additionwas added
2. stirringthe mixture was stirred at room temperature for 6 hr
3. filtrationThe insoluble material was filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionThe obtained residue was diluted with ethyl acetate (100 mL)/tetrahydrofuran (10 mL)
6. washwashed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThe insoluble material was filtered off
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe obtained residue was triturated with ethyl acetate and diisopropyl ether

ORD record

ord-c797a762040845b0b1466e35a02e789a

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2