Diisopropylethylamine → HCID 68525447, 화합물

To a solution of 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxyfuran-3-carboximidamide (0.14 g, 0.50 mmol) that was obtained in Example 1 (1d) and 4-phenyl-5-(trifluoromethyl)thiophene-2-carbonyl chloride (0.17 g, 0.60 mmol) in dichloromethane (10 ml) was added N,N-diisopropylethylamine (0.17 ml, 1.0 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 1 hour. After stirring, a saturated aqueous solution of sodium hydrogencarbonate (1.0 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was poured into water (20 ml) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo. Subsequently, to a solution of the residue obtained in tetrahydrofuran (1.0 ml) was added tetrabutylammonium fluoride (a 1.0 M solution in tetrahydrofuran, 0.75 ml, 0.75 mmol) with stirring, and the resulting mixture was stirred at 60° C. for 3 hours. After stirring, the reaction mixture was poured into water (20 ml) to quench the reaction and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (0.20 g) in a yield of 10% as a white crystalline solid.

1. stirringthe resulting mixture was stirred for 1 hour
2. stirringAfter stirring
3. customto quench
4. customthe reaction
5. extractionextracted with ether
6. washThe extract was washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over magnesium sulfate
8. filtrationAfter filtration
9. customthe filtrate was evaporated in vacuo
10. customSubsequently, to a solution of the residue obtained in tetrahydrofuran (1.0 ml)
11. stirringwith stirring
12. stirringthe resulting mixture was stirred at 60° C. for 3 hours
13. stirringAfter stirring
14. customto quench
15. customthe reaction
16. extractionextracted with ether
17. washThe extract was washed with a saturated aqueous solution of sodium chloride
18. dry with materialdried over magnesium sulfate
19. filtrationAfter filtration
20. customthe filtrate was evaporated in vacuo

ORD 기록

ord-70ad4a52cef24979821ad341bbcf25f9

출처 데이터셋

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07687491B2