Benzoyl chloride → N-(1-Benzoyl-8-chloro-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

Temperatur

50 °C

To a solution of compound 163A (164 mg, 0.472 mmol) in pyridine (1 mL) and CH2Cl2 (1 my) at RT was added benzoyl chloride (82 μL, 0.71 mmol), and the mixture was then stirred at 50° C. for 16 h. After cooling to RT, the reaction was concentrated in vacuo and the resultant residue was taken into MeOH (4 mL), and Et3N (1 mL) added. The reaction was stirred at 70° C. for 1 h. After cooling to RT, the reaction was concentrated. The residue was diluted with 10% aqueous citric acid, then extracted with EtOAc (3×15 mL). The combined EtOAc extracts were concentrated. The resulting residue was purified using preparative HPLC (YMC S5 ODS 20×100 mm) eluting with MeOH (50-80%) in H2O for 8 min, and then 80% MeOH in H2O for 7 min to give the title compound (60 mg, 28%) as a white solid. HPLC: 99% at 6.2 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A 90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 452 [M+H]+.

1. temperatureAfter cooling to RT
2. concentrationthe reaction was concentrated in vacuo
3. additionadded
4. stirringThe reaction was stirred at 70° C. for 1 h
5. temperatureAfter cooling to RT
6. concentrationthe reaction was concentrated
7. additionThe residue was diluted with 10% aqueous citric acid
8. extractionextracted with EtOAc (3×15 mL)
9. concentrationThe combined EtOAc extracts were concentrated
10. customThe resulting residue was purified
11. washeluting with MeOH (50-80%) in H2O for 8 min

ORD-Eintrag

ord-f500c41fa29340d1a06a988a3ce7bcb4

Quelldatensatz

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07884113B2