2,4-Pyridinedicarbonitrile → HCID 178510202, Verbindung

HRID 1455314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455314
[C:1]([C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][N:4]=1)#[N:2].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=2)(N)[C@@H:44]([NH2:50])[CH2:45][O:46]COC)=[CH:39][CH:38]=1>C1(C)C=CC=CC=1>[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]2[NH:50][C@@H:44]([CH2:45][OH:46])[C:43]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)([C:52]3[CH:53]=[CH:54][C:55]([F:58])=[CH:56][CH:57]=3)[N:2]=2)[CH:8]=1)#[N:10]

Komponenten

5

Edukt 3

HCID 1201442,4-PyridinedicarbonitrileHCID 2733225Ytterbium triflateHCID 44139233(2R)-1,1-bis(4-fluorophenyl)-3-methoxymethoxy-1,2-propanediamine

Produkt 1

HCID 178510202HCID 178510202, VerbindungAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2,4-Dicyanopyridine (601 mg) and ytterbium trifluoromethanesulfonate (289 mg) were added to a solution of (2R)-1,1-bis(4-fluorophenyl)-3-(methoxymethoxy)-1,2-propanediamine (1.50 g) in toluene (30 mL), and the mixture was refluxed under stirring for 2 days. The reaction mixture was concentrated in vacuo, and then the residue was dissolved in tetrahydrofuran (20 mL). 6N Hydrochloric acid (10 mL) was added to the solution, and then the mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated in vacuo, and then the residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=2:1) to give the objective compound (385 mg).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in tetrahydrofuran (20 mL)
  4. addition6N Hydrochloric acid (10 mL) was added to the solution
  5. stirringthe mixture was stirred at room temperature for 24 hours
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-11a5cdee481e47f9900b3ba771221dfc
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482358B2

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