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Guanidine Hydrochloride → HCID 178479502, Verbindung

HRID 1869155
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1869155
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]([C:37]([F:40])([F:39])[F: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]([C:37]([F:39])([F:38])[F:40])[CH:35]=3)[N:30]=[CH:29][CH:28]=2)[CH:19]=1)=[O:17])[C:6]([NH2:8])=[NH:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 5742Guanidine HydrochlorideHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 865947963-chlorocarbonyl-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride

Produkt 1

HCID 178479502HCID 178479502, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
2×
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

20 cm3 of methanol and 20 cm3 (10 mmol) of a 0.5M solution of sodium methoxide in methanol are added to 0.955 g (10 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 0.75 g (2 mmol) of 3-chlorocarbonyl-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride, suspended in 20 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 solid obtained is triturated in 20 cm3 of isopropyl ether and filtered off, resulting in 0.54 g of 3-guanidinocarbonyl-1-(6-(trifluoromethyl)quinol-4-yl)-1H-indole hydrochloride in the form of a white powder melting at 260° C. Mass spectrum (EI): m/e 397 (M+•), m/e 339 (base peak).

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 solid obtained
  11. customis triturated in 20 cm3 of isopropyl ether
  12. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-e8046a7648934e4982679387ece12805
Quelldatensatz
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07638521B2

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