Water → Ethyl 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionate

HRID 2370941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2370941
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Br[CH2:23][C:24]#[C:25][CH3:26].O>CN(C=O)C>[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][N:20]([CH2:23][C:24]#[C:25][CH3:26])[CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 178470993HCID 178470993, Verbindung

Produkt 1

HCID 69331513Ethyl 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

11 mg (0.23 mmol, 50%) of sodium hydride were added to a solution of 60 mg (0.23 mmol) of ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate (example 1g) in 0.5 ml of DMF at RT and stirred for 1 h. Then 31 mg (37 μl, 0.23 mmol) of 1-bromo-2-butine were added, and the mixture was stirred at RT for 1 h. 1 ml of water was then added and the mixture was extracted with EA. The organic phase was dried over Na2SO4, filtered and concentrated. Chromatography of the residue on silica gel afforded 28 mg of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at RT for 1 h
  2. extractionthe mixture was extracted with EA
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-df2fdcbaa70d4f1c8ed1c6542051fd19
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710232B2

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