1,1,1-Trimethoxy-2-chloroethane → 2-Chloromethyl-1-ethyl-6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246457
[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[Cl:26][CH2:27][C:28](OC)(OC)OC.[NH2:35][C:36]1[C:37]([C:55]#[N:56])=[N:38][C:39]([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:53])[F:52])[CH:46]=2)=[CH:40][C:41]=1[NH:42][CH2:43][CH3:44]>C(#N)C>[Cl:26][CH2:27][C:28]1[N:42]([CH2:43][CH3:44])[C:41]2[CH:40]=[C:39]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([C:51]([F:54])([F:52])[F:53])[CH:46]=3)[N:38]=[C:37]([C:55]#[N:56])[C:36]=2[N:35]=1

Komponenten

5

Edukt 3

HCID 1447021,1,1-Trimethoxy-2-chloroethaneHCID 2733225Ytterbium triflateHCID 685171643-Amino-4-ethylamino-6-(3-trifluoromethylphenyl)-pyridine-2-carbonitrile

Produkt 1

HCID 685169312-Chloromethyl-1-ethyl-6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ytterbium triflate (1.16 g, 1.8 mmol) and 2-chloro-1,1,1-trimethoxyethane (7.56 mL, 56.0 mmol) was added to a solution of 3-amino-4-ethylamino-6-(3-trifluoromethylphenyl)-pyridine-2-carbonitrile (5.73 g, 18.7 mmol) in acetonitrile (150 mL). The mixture was refluxed for 48 hours, then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether, filtered off to afford the title compound (5.92 g, 87%) as a solid. 1H NMR (DMSO-d6) δ: 8.85 (s, 1H); 8.50-8.00 (m, 2H); 7.90-7.70 (m, 2H); 5.26 (s, 2H); 4,55-4.45 (m, 2H); 1.48 (t, J=7 Hz, 3H). MS m/z: 365 (M+1).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 48 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered off

Quellen und Nachweise

ORD-Eintrag
ord-b7415f9f57fc40bdad8908c685e69f13
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687515B2

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