HCID 86623876, compound → HCID 59825673, compound

Participants

Reaction Steps

4-[5-(1H-Benzimidazol-2-ylsulfanyl)-furan-2-yl]-1,4,6,7,8,9-hexahydro-pyrazolo[3,4-b]quinolin-5-one (162 mg) was resolved via preparative chiral HPLC (column: Pirkle Whelk 01 SS 10 μm 730 g 350×60 mm; eluting solvent: n-heptane/2-propanol/methanol 50/40/10 v/v/v+0.1% triethylamine; rate: 90-125 mL/min; detection=254 nm). 69 mg of (+)-9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester were obtained as a crystalline pale-yellow powder. MS El: m/z 403: [M]+ m/z 187: [M]+ —C11H7N2OS (base peak) m/z 159: 187 —CO. Enantiomeric purity (chiral HPLC column: Pirkle Whelk 01 SS 10 μm 250×4.6 mm; eluting solvent: n-heptane/2-propanol/methanol 50/40/10 v/v/v+0.1% triethylamine; rate: 1 mL/min; detection=254 nm): >99%. αD=+215.50° +/−2.9 (c=1.991 mg/0.5 mL CH3OH). 84 mg of (−)-9-[5-(1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester were obtained as a crystalline pale-yellow powder. MS El: m/z 403: [M]+ m/z 254: [M]+ —C7H5N2S (base peak); m/z 187: 254 —C4H2O. Enantiomeric purity: >98%. αD=−204.70° +/−2.7 (c=2.190 mg/0.5 mL CH3OH).

Provenance & Evidence