Potassium bis(trimethylsilyl)amide → 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid methyl ester

HRID 2212191

Reaktionsgleichung

Reaktionsgleichung von HRID 2212191
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][O:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([NH:21][C:22]([C:24]2[C:25]([C:30]3[C:35](F)=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:37])=[N:26][O:27][C:28]=2[CH3:29])=[O:23])[CH2:16]1)=[O:14]>CN(C)C=O>[CH3:11][O:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([N:21]2[C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=3[C:25]3=[N:26][O:27][C:28]([CH3:29])=[C:24]3[C:22]2=[O:23])[CH2:16]1)=[O:14]

Komponenten

4

Edukt 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69652389HCID 69652389, Verbindung

Produkt 1

HCID 99515613-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid methyl esterAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Add potassium bis(trimethylsilyl)-amide (5.5 mL, 2.73 mmol, 0.5 M in toluene) to a solution of 3-{[3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-piperidine-1-carboxylic acid methyl ester (0.72 g, 1.82 mmol) in dimethylformamide (56 mL). After 5 minutes, quench the reaction with 1N HCl and concentrate. Partition the resulting material between 20% isopropanol/chloroform and 1N HCl. Wash the organic layer with saturated aqueous sodium bicarbonate solution and brine, dry over magnesium sulfate, and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform) to give 632 mg of the title compound as a white solid, 92% yield. 1H NMR: consistent with structure. MS (ion spray) 376 (M+).

Aufarbeitung

  1. customquench
  2. customthe reaction with 1N HCl
  3. concentrationconcentrate
  4. customPartition the resulting material between 20% isopropanol/chloroform and 1N HCl
  5. washWash the organic layer with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdry over magnesium sulfate
  7. concentrationconcentrate
  8. customPurify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-98d59a58ccf449549ce5dfcde00cd7cb
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101891B2

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