Potassium Carbonate → 2-acetyl-7-chloro-3-[4-(4-hydroxypiperidine-1-sulfonyl)-benzyl]-1-phenyl-1H-quinolin-4-one

HRID 1697089

反応式

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:20](=[O:39])[CH2:21][CH2:22][C:23]2[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:31])=[O:30])=[CH:25][CH:24]=2)=[C:6]([N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9](=O)[C:10](=[O:12])[CH3:11])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:10]([C:9]1[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]2[C:5]([C:20](=[O:39])[C:21]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([N:32]3[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]3)(=[O:31])=[O:30])=[CH:27][CH:28]=1)=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=2)(=[O:12])[CH3:11]

参加物

反応条件

温度: 80 °C

実験手順

To N-(5-chloro-2-{3-[4-(4-hydroxypiperidine-1-sulfonyl)-phenyl]-propionyl}-phenyl)-2-oxo-N-phenyl-propionamide in MeOH 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 15-20 min; 100% EtOAc 22-35 min) to provide 2-acetyl-7-chloro-3-[4-(4-hydroxypiperidine-1-sulfonyl)-benzyl]-1-phenyl-1H-quinolin-4-one (compound 70). Mp=145.5-147.2° C.; M+H 551.

後処理

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 15-20 min; 100% EtOAc 22-35 min)

出典と根拠

ORDレコード: ord-a6f655b445d240e496b4ad5c96638f30
出典データセット: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08163906B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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