Water → Ethyl 3-(6-aminopyridin-3-yl)-2-[1-(2-oxo-1-phenylpyrrolidin-3-yl)-1H-imidazol-4-yl]-propionate

HRID 2370921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2370921
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:23]1[CH2:27][CH2:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]1=[O:34].O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH:23]3[CH2:27][CH2:26][N:25]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:24]3=[O:34])[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 34652323-Bromo-1-phenylpyrrolidin-2-oneHCID 178470993HCID 178470993, Verbindung

Produkt 1

HCID 69330945Ethyl 3-(6-aminopyridin-3-yl)-2-[1-(2-oxo-1-phenylpyrrolidin-3-yl)-1H-imidazol-4-yl]-propionateAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 60.1 mg (0.23 mmol) of the compound from example 1g in 1 ml of absolute DMF was mixed with 11 mg (0.23 mmol) of sodium hydride (50%) and stirred at RT for 1 h. Then 55.5 mg (0.23 mmol) of (+/−)-3-bromo-1-phenyl-2-pyrrolidinone were added, and the mixture was stirred at RT for 45 min. The reaction solution was mixed with 1 ml of water and extracted several times with EA. The combined EA extracts were dried over Na2SO4, filtered and concentrated. Purification of the resulting residue by chromatography on silica gel with CH2Cl2/methanol (92:8 to 85:15 in 35 min) as mobile phase afforded 52.2 mg of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at RT for 45 min
  2. extractionextracted several times with EA
  3. dry with materialThe combined EA extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the resulting residue by chromatography on silica gel with CH2Cl2/methanol (92:8 to 85:15 in 35 min) as mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-d3860a4c39ce4660be2d24dc02934a79
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710232B2

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