Trifluoromethanesulfonic anhydride → 5-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-furan-2-carbonitrile

HRID 1421711

Reaktionsgleichung

Reaktionsgleichung von HRID 1421711
O[CH2:2][C:3]1[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14](=[O:48])[N:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]3[N:25]=[CH:26][N:27](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:28]=3)=[CH:19][N:18]=2)[CH:16]=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14](=[O:48])[N:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]3[N:25]([CH2:2][C:3]4[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=4)[CH:26]=[N:27][CH:28]=3)=[CH:19][N:18]=2)[CH:16]=1

Komponenten

6

Edukt 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 30214065-(Hydroxymethyl)furan-2-carbonitrileHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Produkt 1

HCID 187797255-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-furan-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of the alcohol from step 2 (0.017 g, 0.137 mmol), 5-chloro-5'-(1-triphenylmethyl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (0.0758 g, 0.143 mmol) and diisopropylethylamine (0.047 mL, 1.49 mmol) in dichloromethane (1.3 mL) at -78° C. was added trifluoromethanesulfonic anhydride (0.023 mL, 0.136 mmol) and the mixture stirred at -78° C. for 1 hour. The mixture was allowed to warm to 0° C. and stirred for 2 hours. The solvent was evaporated in vacuo. The residue was dissolved in methanol (1 mL), heated at reflux for 2 hour, and the solvent evaporated in vacuo. The residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was dried, (Na2SO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 1:99 to 3:97 MeOH:CH2Cl2) to afford the title compound as a white solid.

Aufarbeitung

  1. temperatureto warm to 0° C.
  2. stirringstirred for 2 hours
  3. customThe solvent was evaporated in vacuo
  4. dissolutionThe residue was dissolved in methanol (1 mL)
  5. temperatureheated
  6. temperatureat reflux for 2 hour
  7. customthe solvent evaporated in vacuo
  8. customThe residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  9. customThe organic layer was dried
  10. custom(Na2SO4) and the solvent evaporated in vacuo
  11. customThe residue was chromatographed (Silica gel, 1:99 to 3:97 MeOH:CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-96b57237b0bc484cbda69d35c7b80716
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077853

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