Sodium Carbonate → 2-amino-5-(3-bromophenyl)-5-(1-ethyl-5-propionyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-4H-imidazol-4-one

HRID 2220474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220474
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([C:11]2C=[C:14]([C:16](=O)CC)[N:13]([CH2:20]C(F)(F)F)[CH:12]=2)=O)[CH:5]=[CH:6][CH:7]=1.[CH3:26][NH:27][C:28]([NH2:30])=[NH:29].[C:31](=[O:34])([O-])[O-].[Na+].[Na+].CCO[C:40]([CH3:42])=O.[CH2:43]([OH:45])C>C(O)C>[NH2:30][C:28]1[N:27]([CH3:26])[C:43](=[O:45])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)([C:9]2[CH:11]=[C:12]([C:31](=[O:34])[CH2:40][CH3:42])[N:13]([CH2:14][CH3:16])[CH:20]=2)[N:29]=1

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 21584252Ethanol ethylacetateHCID 597727141-(3-bromo-phenyl)-2-[5-propionyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-3-yl]-ethane-1,2-dioneHCID 178485088HCID 178485088, Verbindung

Produkt 1

HCID 159497442-amino-5-(3-bromophenyl)-5-(1-ethyl-5-propionyl-1H-pyrrol-3-yl)-3-methyl-3,5-dihydro-4H-imidazol-4-oneAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(3-bromo-phenyl)-2-[5-propionyl-1-(2,2,2-trifluoro-ethyl)-1H-pyrrole-3-yl]-ethane-1,2-dione (4.5 g, 0.0108 mol), methylguanidine (2.36 g, 0.0216 mol) and sodium carbonate (2.28 g, 0.0216 mol) in 100 ml ethanol is heated to reflux for three hours. The solvent is evaporated to dryness and the residue is flash chromatographed on silica gel with eluent EtOAc/Ethanol (containing 2 mol ammonia) to afford the product 3.8 gram (75%) as an off-white solid, mp 100-102° C.,

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for three hours
  3. customThe solvent is evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3d6fc21eb5b045828b640ca9d790f444
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417047B2

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