Potassium Carbonate → HCID 25118715, compound

HRID 1697087Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:40])[C:4]([N:6]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:39])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]2[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:2][C:3]([C:4]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:13]2[C:14]([C:20](=[O:39])[C:21]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]3[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]3)(=[O:30])=[O:31])=[CH:25][CH:24]=1)=[CH:15][CH:16]=[C:17]([Cl:19])[CH:18]=2)=[O:40]

Participants

Conditions

Temperature: 80 °C

Procedure

To N-(5-chloro-2-{3-[4-(4-hydroxypiperidine-1-sulfonyl)-phenyl]-propionyl}-phenyl)-N-phenyl-oxalamic acid methyl ester (0.40 g) in MeOH (15 mL) was added K2CO3 (0.096 g), and the mixture heated at 80° C. for 1.5 h, then concentrated. The residue was taken up in EtOAc/H2O, and the aqueous layer washed with EtOAc (2×25 mL). The combined organic layers were dried over Na2SO4, and the solvent removed under reduced pressure. The residue was chromatographed on anhydrous silica (20% EtOAc/hexanes 0-5 min; 60% EtOAc/hexanes 6-10 min; 100% EtOAc 11-40 min) to provide 7-chloro-3-[4-(4-hydroxypiperidine-1-sulfonyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester (compound 69). M+H 567; mp=170.0-171.0° C.

Workup

concentrationconcentrated
washthe aqueous layer washed with EtOAc (2×25 mL)
dry with materialThe combined organic layers were dried over Na2SO4
customthe solvent removed under reduced pressure
customThe residue was chromatographed on anhydrous silica (20% EtOAc/hexanes 0-5 min; 60% EtOAc/hexanes 6-10 min; 100% EtOAc 11-40 min)

Sources & evidence

ORD record: ord-d7c69de82c30496992362a26d72866ab
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163906B2

Reaction notes

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