反应详情

Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (700 mg, 1.56 mmol) was stirred in EtOH (20 mL). To this suspension was added solid NaOH (624 mg, 15.6 mmol), followed by water (10 mL). The flask was then fitted with a condenser and was heated to reflux for 2 h. When TLC analysis showed that the reaction was complete, the mixture was cooled to room temperature and diluted with water. The product was extracted with dichloromethane (3×) and the combined organics were dried, filtered and concentrated, then chromatographed in EtOAc, followed by 10% 2M NH3/MeOH in dichloromethane. The isolated spot was then triturated with methanol and ether. Yield (223 mg, 43%). 1H NMR (DMSO-d6) δ 7.73 (d, 1H, J=3.6 Hz), 7.59 (d, 1H, J=5.4 Hz), 7.10 (m, 2H), 6.73 (m, 2H), 6.45 (brs, 2H), 3.91 (t, 1H, J=7.2 Hz), 2.81 (t, 1H, J=7.2 Hz), 2.65 (t, 1H, J=7.2 Hz), 2.50 (t, 1H, J=7.2 Hz); ESI-MS (m/z, %): 329 (MH+, 70), 149 (100), 141 (80), 127 (96).

1. customThe flask was then fitted with a condenser
2. temperaturewas heated
3. temperatureto reflux for 2 h
4. extractionThe product was extracted with dichloromethane (3×)
5. customthe combined organics were dried
6. filtrationfiltered
7. concentrationconcentrated
8. customchromatographed in EtOAc
9. customThe isolated spot was then triturated with methanol and ether
10. customYield (223 mg, 43%)