Sodium hydride → 6-chloro-4'-{5-chloro-2-[1-(4-fluoro-benzenesulfonylaminocarbonyl)-cyclobutoxy]-phenyl}-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504454

Reaktionsgleichung

Reaktionsgleichung von HRID 504454
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]4([C:28](O)=[O:29])[CH2:27][CH2:26][CH2:25]4)[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[F:53][C:54]1[CH:59]=[CH:58][C:57]([S:60]([NH2:63])(=[O:62])=[O:61])=[CH:56][CH:55]=1.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:40])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]4([C:28]([NH:63][S:60]([C:57]5[CH:56]=[CH:55][C:54]([F:53])=[CH:59][CH:58]=5)(=[O:61])=[O:62])=[O:29])[CH2:27][CH2:26][CH2:25]4)[CH2:14][C:13](=[O:31])[NH:12][CH:11]3[C:32]3[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=3[CH3:39])[C:5]2=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 1202314-FluorobenzenesulfonamideHCID 765681536-chloro-4'-[5-chloro-2-(1-hydroxycarbonyl-cyclobutoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Produkt 1

HCID 749287446-chloro-4'-{5-chloro-2-[1-(4-fluoro-benzenesulfonylaminocarbonyl)-cyclobutoxy]-phenyl}-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneAusbeute 31,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-hydroxycarbonyl-cyclobutoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (50 mg, 0.086 mmol) and CDI (28 mg, 0.17 mmol) in DMF (0.5 mL) was heated at 60° C. for 30 min, and then cooled to root temperature. To this solution was added a mixture of 4-fluoro-benzenesulfonamide (175 mg, 1 mmol) and NaH (40 mg, 60%, 1 mmol) in DMF (1 mL). The resulting mixture was stirred at room temperature for 10 min, purified by prep-HPLC to give the title compound as a white solid (20 mg).

Aufarbeitung

  1. temperaturecooled
  2. additionTo this solution was added
  3. custompurified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b722728afcdd4cfe81b2ccac998723c4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776875B2

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