Potassium Carbonate → Methyl 5-(5-(dimethylcarbamoyl)-1H-imidazol-2-yl)-2,4-dimethylbenzoate

HRID 541384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541384
Br[CH2:2][C:3](=O)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].Cl.[C:11]([C:14]1[C:15]([CH3:25])=[CH:16][C:17]([CH3:24])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20])(=[NH:13])[NH2:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:7][N:6]([CH3:8])[C:4]([C:3]1[NH:13][C:11]([C:14]2[C:15]([CH3:25])=[CH:16][C:17]([CH3:24])=[C:18]([CH:23]=2)[C:19]([O:21][CH3:22])=[O:20])=[N:12][CH:2]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 68288602Methyl 5-carbamimidoyl-2,4-dimethylbenzoate hydrochloride2×HCID 866725393-bromo-N,N-dimethyl-2-oxopropanamide

Produkt 1

HCID 68288243Methyl 5-(5-(dimethylcarbamoyl)-1H-imidazol-2-yl)-2,4-dimethylbenzoateAusbeute 29,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-N,N-dimethyl-2-oxopropanamide (246 mg), methyl 5-carbamimidoyl-2,4-dimethylbenzoate hydrochloride (compound 2.5, 237 mg), and potassium carbonate (311 mg) in acetonitrile (12 ml) was heated to reflux for 48 hours. After cooling to ambient temperature the mixture was concentrated. The residue was dissolved in EtOAc and washed with brine, dried over MgSO4, concentrated, and purified by flash chromatography (SiO2; EtOAc) to give 88 mg of the title compound. m/z (ES+) 302 (M+H)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. concentrationwas concentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography (SiO2; EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-53ae08d66e294c97920442843f604e5d
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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