反应详情

To a stirred solution of N-(4-chlorophenyl)-2-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetyl)hydrazinecarbothioamide (0.2 g, 0.49 mmol) in dry DMF (10 mL) at room temperature, EDC HCl (0.189 g, 0.98 mmol) and TEA (0.148 g 1.4 6 mmol) were added. The reaction was stirred at room temperature overnight and monitored by LCMS. The solvent was removed under vacuum and then water (20 mL) was added to the residue. The solid which formed was filtered, dried, and the crude product (0.15 g) was recrystallized in a mixture of ethanol/ACN to afford 6-((5-(4-chlorophenylamino)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (70 mg, 38%) as an off white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 2.41 (t, J=7.20 Hz, 2H), 2.85 (t, J=8.00 Hz, 2H), 5.23 (s, 2H), 6.80 (d, J=8.40 Hz, 1H), 6.87 (dd, J=2.80, 8.40 Hz, 1H), 6.94 (d, J=2.40 Hz, 1H), 7.42 (dd, J=2.00, 6.80 Hz, 2H), 7.58 (dd, J=2.40, 6.80 Hz, 2H), 9.96 (s, 1H), 10.77 (s, 1H). LCMS: RT 1.50 min, LCMS (ES-API), m/z 371.0 (M+H).

1. customThe solvent was removed under vacuum
2. additionwater (20 mL) was added to the residue
3. customThe solid which formed
4. filtrationwas filtered
5. customdried
6. customthe crude product (0.15 g) was recrystallized in a mixture of ethanol/ACN