N-Iodosuccinimide → 7-Cyclobutyl-5-iodo-3H-imidazo[5,1-f][1,2,4]triazin-4-one

HRID 422643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 422643
[CH:1]1([C:5]2[N:13]3[C:8]([C:9](=[O:14])[NH:10][CH:11]=[N:12]3)=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[I:15]N1C(=O)CCC1=O>CN(C=O)C>[CH:1]1([C:5]2[N:13]3[C:8]([C:9](=[O:14])[NH:10][CH:11]=[N:12]3)=[C:7]([I:15])[N:6]=2)[CH2:2][CH2:3][CH2:4]1

Komponenten

4

Edukt 2

HCID 120273N-Iodosuccinimide2×HCID 1359932727-cyclobutyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one

Produkt 1

HCID 1360179687-Cyclobutyl-5-iodo-3H-imidazo[5,1-f][1,2,4]triazin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A solution of 7-cyclobutyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one (789 mg, 4.15 mmol) and N-iodosuccinimide (933 mg, 4:15 mmol) in anhydrous DMF (40 mL) was stirred overnight at rt. An additional 4 equiv of NIS was added and reaction was heated to 55° C. for 6 h. The reaction mixture was concentrated in vacuo and partitioned between DCM and H2O and separated. The aqueous layer was washed with DCM (3×) and the combined organic fractions were washed with 1M sodium thiosulfate (Na2S2O3) (1×), brine (1×), dried over sodium sulfate (Na2SO4), filtered, and concentrated in vacuo. The solid was triturated with 20% EtOAc in DCM and filtered through a fritted Buchner funnel resulting in the title compound as an off-white solid; 1H NMR (DMSO-d6, 400 MHz) δ 1.84-1.96 (m, 1H), 1.98-2.13 (m, 1H), 2.25-2.43 (m, 4H), 3.84-3.96 (m, 1H), 7.87 (s, 1H); MS (ES+): m/z 317.02 (100) [MH+], HPLC: tR=2.62 min (MicromassZQ, polar—5 min).

Aufarbeitung

  1. customreaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between DCM and H2O
  4. customseparated
  5. washThe aqueous layer was washed with DCM (3×)
  6. washthe combined organic fractions were washed with 1M sodium thiosulfate (Na2S2O3) (1×), brine (1×)
  7. dry with materialdried over sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe solid was triturated with 20% EtOAc in DCM
  11. filtrationfiltered through a fritted Buchner funnel

Quellen und Nachweise

ORD-Eintrag
ord-ec0cd89549c34ca0908d1ba3d346d06b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101613B2

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