Diisopropylethylamine → N-[4-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-3-fluorophenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

N-[5-(4-Amino-2-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (240 mg, 0.70 mmol), 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid (190 mg, 0.77 mmol) and HATU (340 mg, 0.91 mmol) were suspended in N,N′-dimethylformamide (3.0 mL), and N,N-diisopropylethylamine (0.24 mL, 1.4 mmol) was added. After stirring at room temperature for 8 hr, the mixture was diluted with ethyl acetate (5.0 mL) and tetrahydrofuran (5.0 mL). The mixture was washed twice with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. The resulting precipitate was collected by filtration to give the title compound (350 mg, 0.61 mmol, 88%) as a pale-yellow solid.

1. washThe mixture was washed twice with saturated aqueous sodium hydrogen carbonate solution
2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
3. customThe solvent was evaporated under reduced pressure, and ethyl acetate
4. additionwas added to the residue
5. filtrationThe resulting precipitate was collected by filtration

ORD 기록

ord-9d4fc6ce4ab146a1b3f3bd54a35f0fdd

출처 데이터셋

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08445509B2