Ammonium Acetate → 6-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester

HRID 79695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79695
[CH3:1][O:2][C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]2[CH:12]([C:15](=O)[NH:16][CH2:17][C:18]([C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=3)=O)[CH2:13][CH2:14][CH:7]2[CH2:6]1)=[O:4].C([O-])(=O)C.[NH4+:32]>>[CH3:1][O:2][C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]2[CH:12]([C:15]3[NH:32][C:18]([C:20]4[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=4)=[CH:17][N:16]=3)[CH2:13][CH2:14][CH:7]2[CH2:6]1)=[O:4]

Komponenten

3

Edukt 2

HCID 517165Ammonium AcetateHCID 666208976-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester

Produkt 1

HCID 666206156-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl esterAusbeute 60 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 6-[2-(4-bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester (110 mg, 0.25 mmol), ammonium acetate (193 mg, 2.5 mmol) and xylenes (8 mL) was heated to 130° C. After 1 hour the mixture was cooled and the xylenes were removed under reduced pressure. Dichloromethane was added to the resulting residue and the mixture was filtered. The solvent was removed under reduced pressure from the filtrate and the resulting residue was subjected to flash chromatography with eluent of(10% methanol in ethyl acetate) and hexane. The product-containing fractions were combined and the solvent was removed under reduced pressure to provide 6-[5-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carboxylic acid methyl ester (65 mg, 0.15 mmol, 60%). C18H19BrN4O3 calculated 418.1 observed [M+H]+ 419.1; rt=1.50 min.

Aufarbeitung

  1. temperatureAfter 1 hour the mixture was cooled
  2. customthe xylenes were removed under reduced pressure
  3. additionDichloromethane was added to the resulting residue
  4. filtrationthe mixture was filtered
  5. customThe solvent was removed under reduced pressure from the filtrate
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c5a76be29633412d90178e0bca6566ec
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841278B2

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