HCID 86623876, compound → HCID 59825673, compound

HRID 1696641Notes

Reaction equation

HRID 1696641 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][C:11]1[O:15][C:14]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][C:18]3N[N:28]=[CH:29][C:17]2=3)=[CH:13][CH:12]=1.CCCCC[CH2:35][CH3:36].[CH3:37][CH:38]([OH:40])C.C[OH:42]>C(N(CC)CC)C>[CH2:38]([O:40][C:35]([C:36]1[NH:28][CH:29]=[C:17]2[CH:16]([C:14]3[O:15][C:11]([S:10][C:2]4[NH:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[CH:12][CH:13]=3)[C:25]3[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=3[NH:19][C:18]=12)=[O:42])[CH3:37]

Participants

4

Reactant 2

HCID 86623876HCID 86623876, compoundHCID 136014549HCID 136014549, compound

Product 1

HCID 59825673HCID 59825673, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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).

Sources & evidence

ORD record
ord-e1ac9a1badde41d8af8fc4876877770f
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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