Potassium Carbonate → (R)-6-((1-(1,3-dioxoisoindolin-2-yl)propan-2-yl)amino)-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile

HRID 340518Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340518
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:15]([F:16])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([NH:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)[N:9]=1.[NH2:28][C@H:29]([CH3:42])[CH2:30][N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41].C(=O)([O-])O.[Na+]>O1CCOCC1>[O:41]=[C:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:39](=[O:40])[N:31]1[CH2:30][C@H:29]([NH:28][C:8]1[C:15]([F:16])=[CH:14][C:11]([C:12]#[N:13])=[C:10]([NH:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)[N:9]=1)[CH3:42]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 28115253(R)-2-(2-aminopropyl)isoindoline-1,3-dioneHCID 866838496-Chloro-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile

Produkt 1

HCID 86683896(R)-6-((1-(1,3-dioxoisoindolin-2-yl)propan-2-yl)amino)-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrileAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Potassium carbonate (115 mg) and 6-chloro-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile (50 mg) were added to a tube containing a 1,4-dioxane (2 ml) solution containing (R)-2-(2-aminopropyl)isoindoline-1,3-dione (52 mg) and the tube was sealed, followed by stirring with heating at 140° C. for 13 hours. The reaction solution was adjusted to room temperature, and a saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:2), and a yellow solid of (R)-6-((1-(1,3-dioxoisoindolin-2-yl)propan-2-yl)amino)-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile (57 mg) was thus obtained.

Aufarbeitung

  1. customthe tube was sealed
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationSubsequently, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:2)

Quellen und Nachweise

ORD-Eintrag
ord-6e1c42e016fb4ad9872ced413b17ad36
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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