Imidazole → HCID 178455042, Verbindung

HRID 632913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632913
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:11]3[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=3)[C:3]=12.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C.O>[Si:27]([O:17][C:13]1[CH:12]=[C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[NH:8][N:9]=2)[CH:16]=[CH:15][CH:14]=1)([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28]

Komponenten

6

Edukt 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 178508710HCID 178508710, Verbindung

Produkt 1

HCID 178455042HCID 178455042, VerbindungAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of compound (2) (4.69 g, 20.66 mmol) and imidazole (2.10 g, 30.99 mmol) in dry DMF (100 mL) was added TBDMSCl (4.70 g, 30.99 mmol). After 16 hr, further aliquots of imidazole (2.10 g, 30.99 mmol) and TBDMSCl (4.70 g, 30.99 mmol) were added and the mixture was stirred for 48 hr. The reaction mixture was diluted with water (120 mL) and extracted with DCM (2×200 mL). The combined organic extracts were washed with water (2×200 mL), dried, filtered and the volume reduced to approximately 100 mL by evaporation in vacuo. The resulting slurry was filtered and the solid washed with heptane (50 mL) to afford the title compound (3) (6.05 g, 85%) as an off-white solid: m/z 343 (M+H)+ (ES+).

Aufarbeitung

  1. extractionextracted with DCM (2×200 mL)
  2. washThe combined organic extracts were washed with water (2×200 mL)
  3. customdried
  4. filtrationfiltered
  5. customthe volume reduced to approximately 100 mL by evaporation in vacuo
  6. filtrationThe resulting slurry was filtered
  7. washthe solid washed with heptane (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-c499c8eff98940e8af5955dfc7b5e1eb
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321773B2

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