1,2-Dichloroethane → HCID 68429731, Verbindung

HRID 335614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335614
[N+:1]([C:4]1[C:12]2[S:11][C:10]([C:13]([OH:15])=O)=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:16](Cl)[CH2:17][Cl:18].[CH:20]1[CH:21]=C[C:23]2[N:28](O)N=[N:26][C:24]=2[CH:25]=1.C(N(CC)CC)C>CN(C=O)C>[ClH:18].[N:28]12[CH2:17][CH2:16][CH:25]([CH2:20][CH2:21]1)[C@@H:24]([NH:26][C:13]([C:10]1[S:11][C:12]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=3[CH:9]=1)=[O:15])[CH2:23]2

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 131624097-Nitrobenzo[b]thiophene-2-carboxylic acid

Produkt 1

HCID 68429731HCID 68429731, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.0 g (8.96 mmol) of 7-nitro-1-benzothiophene-2-carboxylic acid and 1.78 g (8.96 mmol) of R-3-aminoquinuclidine dihydrochloride are initially charged in 25 ml of DMF. At 0° C., 2.06 g (10.75 mmol) of EDC, 1.45 g (10.75 mmol) of HOBt and 4.50 ml (32.26 mmol) of triethylamine are added to the solution. The mixture is stirred at RT for 18 h. The reaction is terminated by addition of a 10% strength aqueous sodium bicarbonate solution, and ethyl acetate is added. The resulting precipitate is filtered off with suction. The mother liquor is extracted twice with ethyl acetate. The organic phases are combined and concentrated. Both the precipitate and the concentrated mother liquor are purified by silica gel column chromatography (mobile phase: dichloromethane/methanol/25% ammonia 100:10:2). The product fractions are concentrated, dissolved in a mixture of methanol and 1N hydrochloric acid, then again concentrated and dried under high vacuum. The resulting solid is triturated with acetonitrile, filtered off with suction and dried at 50° C. under reduced pressure. 1.10 g (32.8% of theory) of the title compound are obtained.

Aufarbeitung

  1. customThe reaction is terminated by addition of a 10% strength aqueous sodium bicarbonate solution, and ethyl acetate
  2. additionis added
  3. filtrationThe resulting precipitate is filtered off with suction
  4. extractionThe mother liquor is extracted twice with ethyl acetate
  5. concentrationconcentrated
  6. customBoth the precipitate and the concentrated mother liquor are purified by silica gel column chromatography (mobile phase: dichloromethane/methanol/25% ammonia 100:10:2)
  7. concentrationThe product fractions are concentrated
  8. dissolutiondissolved in a mixture of methanol and 1N hydrochloric acid
  9. concentrationagain concentrated
  10. customdried under high vacuum
  11. customThe resulting solid is triturated with acetonitrile
  12. filtrationfiltered off with suction
  13. customdried at 50° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e84c934630c14cbb923569db7456b88c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884017B2

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