Potassium Carbonate → HCID 178483669, Verbindung

HRID 526210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526210
C([O:4][CH2:5][C:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]1)=[N:15][C:14]([Cl:29])=[CH:13][CH:12]=2)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:29][C:14]1[N:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:6](=[O:7])[CH2:5][OH:4])=[C:17]2[NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 178476434HCID 178476434, Verbindung

Produkt 1

HCID 178483669HCID 178483669, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclohexylamino}-1,5-naphthyridin-3-yl)-2-oxoethyl acetate (90 mg, 0.22 mmol) in methanol was added freshly ground potassium carbonate (90 mg, 0.65 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with satd. aq. sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the desired product (18 mg, 22%) as a yellow solid. ESI MS m/z 377 [M+H]+.

Aufarbeitung

  1. additionThe reaction mixture was diluted with satd
  2. extractionaq. sodium bicarbonate and extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-26123b82890648a48be893425ababa3d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345709B2

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