Potassium Carbonate → methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylate

HRID 1650999

Reaktionsgleichung

Reaktionsgleichung von HRID 1650999
[CH2:1]1[CH:14]2[CH:5]([CH2:6][C:7]3[C:12]([CH:13]2[NH:15][CH:16]=[N:17][C:18]#[N:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.[C:20](=O)([O-])[O-].[K+].[K+].Br[CH:27](C)[C:28]([O-:30])=[O:29]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[CH2:1]1[CH:14]2[CH:5]([CH2:6][C:7]3[C:12]([CH:13]2[N:15]2[C:27]([C:28]([O:30][CH3:20])=[O:29])=[C:18]([NH2:19])[N:17]=[CH:16]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 14535398Alpha-bromopropionateHCID 178512230HCID 178512230, Verbindung

Produkt 1

HCID 23050704methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 2855718-Crown-6Lösungsmittel

Versuchsvorschrift

20.8 Parts of N-(1,2,3,4,4a,9,9a,10-octahydroanthracene-9-yl)-N'-cyano-formamidine were dissolved in 140 ml of N,N-dimethylformamide together with 0.1 parts of 18-crown-6. 28.4 Parts of potassium carbonate were added. The mixture was heated to +80° C. and 13.8 Parts of α-bromo-methyl-acetate were added. After 15 hours at +80° C. to +100° C. the reactants were poured on ice and the mixture was extracted with ether. The etheral extracts were dried with Na2SO4, filtered and concentrated. 21 Parts of crude residue were chromatographed on a silica gel column and extracted with an ethyl acetate/hexane mixture (1:1). 11.6 Parts (43%) of methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracene-9-yl)-4amino-1H-imidazole-5-carboxylate (int. 15), mp. 155-159° C. were isolated.

Aufarbeitung

  1. temperatureThe mixture was heated to +80° C.
  2. additionAfter 15 hours at +80° C. to +100° C. the reactants were poured on ice
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe etheral extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custom21 Parts of crude residue were chromatographed on a silica gel column
  8. extractionextracted with an ethyl acetate/hexane mixture (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8602da9df2cb4871b69c1d96b50b5e72
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04927449

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