2,4-Pyridinedicarbonitrile → (5S)-2-(4-cyano-2-pyridyl)-4-(4-fluorophenyl)-4-(6-fluoro-3-pyridyl)-5-methyl-2-imidazoline

HRID 1455313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455313
[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:48]2[CH:49]=[N:50][C:51]([F:54])=[CH:52][CH:53]=2)(N)[C@@H:44]([NH2:46])[CH3:45])=[CH:39][CH:38]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1]2[NH:46][C@@H:44]([CH3:45])[C:43]([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)([C:48]3[CH:49]=[N:50][C:51]([F:54])=[CH:52][CH:53]=3)[N:2]=2)[CH:8]=1)#[N:10]

Komponenten

6

Edukt 3

HCID 1201442,4-PyridinedicarbonitrileHCID 2733225Ytterbium triflateHCID 58649654(2S)-1-(4-fluorophenyl)-1-(6-fluoro-3-pyridyl)-1,2-propanediamine

Produkt 1

HCID 178461606(5S)-2-(4-cyano-2-pyridyl)-4-(4-fluorophenyl)-4-(6-fluoro-3-pyridyl)-5-methyl-2-imidazolineAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2,4-Dicyanopyridine (46.5 mg) and ytterbium trifluoromethanesulfonate (24 mg) were added to a solution of the optical active (2S)-1-(4-fluorophenyl)-1-(6-fluoro-3-pyridyl)-1,2-propanediamine (100 mg) described in Reference Example 5-1 in toluene (0.25 mL), and the mixture was stirred at 100° C. for 5 hours. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution in this order, and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and the organic solvent was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=2:3) to give the objective compound (106 mg) as a white solid.

Aufarbeitung

  1. washwashed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution in this order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customSodium sulfate was removed by filtration
  4. customthe organic solvent was evaporated in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (C-300; hexane: ethyl acetate=2:3)

Quellen und Nachweise

ORD-Eintrag
ord-f3f7177c30c1402aa87329096b13a18c
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482358B2

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