Sodium Hydroxide → HCID 59825635, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 330 mg (0.657 mmol) of 9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester in 10 ml ethanol and 1 ml water was added 263 mg of sodium hydroxide in a round bottom flask. The reaction mixture was heated at 40° C. with stirring for 8 hours, and at 30° C. overnight. Water was added to the reaction mixture and it was extracted twice with ethyl acetate. The organic layers were washed with water and brine and dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oily residue was dissolved in 1 ml methanol and 14 ml of dichloromethane and purified by chromatography on a prepacked 75 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/methanol from 98/2 to 92/8 v/v in 50 min; rate: 40 mL/min). The fractions containing the desired product were combined and concentrated to dryness under reduced pressure giving 106 mg of 9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-6,6-dimethyl-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid (34% yield). Analytical LC/MS method B: [M+H]+=475.5; retention time: 3.01 min; 95% UV purity. 300 MHz 1H NMR (DMSO-d6) δ (ppm): 0.91 (s, 3H); 0.98 (s, 3H); 2.05 (d, J=17.0 Hz, 1H); 2.16 (d, J=17.0 Hz, 1H); 2.50 (d partially masked, J=17.0 Hz, 1H); 2.61 (d, J=17.0 Hz, 1H); 5.14 (s, 1H); 5.97 (d, J=3.5 Hz, 1H); 6.73 (d, J=3.0 Hz, 1H); 6.83 (d, J=3.5 Hz, 1H); de 7.10 à 7.20 (m, 2H); 7.40 (d large, J=8.0 Hz, 1H); 7.52 (d large, J=8.0 Hz, 1H); 8.32 (s large, 1H); 11.3 (s large, 1H); 12.25 (m wide, 1H); 12.3 (s large, 1H).

Provenance & Evidence