반응 #2487482

반응 방정식

water

6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime

1,1′-thiocarbonyldiimidazole

→

title compound

3-[6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridin-2-yl]-4,5-dihydro-1,2,4-thiadiazol-5-one

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   추출followed by extraction with ethyl acetate
2. 2
   세척The organic layer was washed with water
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   농축concentrated under reduced pressure
5. 5
   workup.ADDITIONTo the residue was added tetrahydrofuran (2 mL), and subsequently boron trifluoride ethyl ether complex (0.21 mL)
6. 6
   workup.ADDITIONwas added
7. 7
   온도under ice-cooling
8. 8
   workup.STIRRINGThe mixture was stirred at room temperature for 3 days
9. 9
   workup.ADDITIONTo the reaction mixture was added water
10. 10
    추출followed by extraction with ethyl acetate
11. 11
    세척The organic layer was washed with 1 mol/L hydrochloric acid and water successively
12. 12
    건조dried over anhydrous magnesium sulfate
13. 13
    농축concentrated under reduced pressure
14. 14
    기타The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol)

실험 절차

To a solution of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime (123 mg) in tetrahydrofuran (2 mL) was added 1,1′-thiocarbonyldiimidazole (71 mg). This mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the residue was added tetrahydrofuran (2 mL), and subsequently boron trifluoride ethyl ether complex (0.21 mL) was added thereto under ice-cooling. The mixture was stirred at room temperature for 3 days. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and water successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol) to obtain the title compound (24 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.55 (2H, s), 6.45-6.55 (1H, m), 6.60-6.70 (1H, m), 6.77 (1H, dd, J=2.5, 8.9 Hz), 7.14 (1H, d, J=2.5 Hz), 7.28 (1H, d, J=8.9 Hz), 7.35-7.60 (5H, m), 7.75-7.95 (2H, m), 13.35 (1H, br s). ESI-MS (m/z): 415 (M+H)+

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