Guanidine Hydrochloride → HCID 178487881, Verbindung

HRID 1869167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869167
C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].O1CCCC1.Cl.[Cl:15][C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=3)[N:30]=[CH:29][CH:28]=2)[CH:19]=1)=[O:17]>CO.ClCCl>[ClH:15].[NH:7]([C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:37][CH3:38])[CH:35]=3)[N:30]=[CH:29][CH:28]=2)[CH:19]=1)=[O:17])[C:6]([NH2:8])=[NH:5]

Komponenten

7

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 865948023-chlorocarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole hydrochloride

Produkt 1

HCID 178487881HCID 178487881, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

20 cm3 of methanol and 17 cm3 (8.5 mmol) of a 0.5M solution of sodium methoxide in methanol are added to 0.812 g (8.5 mmol) of guanidine hydrochloride under an argon atmosphere. After stirring at a temperature in the region of 25° C. for 1 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is three times successively dissolved in 20 cm3 of dichloromethane and evaporated to dryness under reduced pressure (2.7 kPa). 40 cm3 of tetrahydrofuran and 0.67 g (1.79 mmol) of 3-chlorocarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole hydrochloride, suspended in 40 cm3 of dichloromethane, are subsequently added thereto under an argon atmosphere. After stirring at a temperature in the region of 20° C. for 16 hours, the reaction mixture is concentrated to give a solid which is purified by flash chromatography [eluent: ethyl acetate/methanol (9/1 and then 8/2 by volume)]. After concentrating the fractions to dryness under reduced pressure (2.7 kPa), the product obtained is triturated in 20 cm3 of isopropyl ether and filtered off, resulting in 0.37 g of 3-guanidinocarbonyl-1-(6-methoxyquinol-4-yl)-1H-indole hydrochloride in the form of a white powder melting at 266° C. Mass spectrum (EI): m/e 359 (M+•), m/e 301.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. dissolutionsuccessively dissolved in 20 cm3 of dichloromethane
  3. customevaporated to dryness under reduced pressure (2.7 kPa)
  4. additionare subsequently added
  5. stirringAfter stirring at a temperature in the region of 20° C. for 16 hours
  6. concentrationthe reaction mixture is concentrated
  7. customto give a solid which
  8. customis purified by flash chromatography [eluent
  9. concentrationAfter concentrating the fractions to dryness under reduced pressure (2.7 kPa)
  10. customthe product obtained
  11. customis triturated in 20 cm3 of isopropyl ether
  12. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-0f21f2b794f84b2d997162e4896971f6
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638521B2

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