ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate → HCID 178507209, Verbindung

HRID 353803

Reaktionsgleichung

Reaktionsgleichung von HRID 353803
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][C:21]([O:23]CC)=O.[NH2:26][C:27]1[NH:31][CH:30]=[N:29][C:28]=1[C:32]#[N:33]>C1COCC1>[NH2:33][C:32]1[C:28]2[N:29]=[CH:30][NH:31][C:27]=2[NH:26][C:21](=[O:23])[C:20]=1[C:12]1[NH:11][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=1

Komponenten

5

Edukt 3

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 2733832Lithium HexamethyldisilazideHCID 178510601HCID 178510601, Verbindung

Produkt 1

HCID 178507209HCID 178507209, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

LiHMDS (4.4 eq) was added to ethyl 1H-benzimidazol-2-ylacetate (1.0 eq) and 5-amino-1H-imidazole-4-carbonitrile (1.0 eq) in THF at 0° C. After 1 hour, the resulting mixture was warmed to room temperature and then stirred overnight. The mixture was quenched with an aqueous saturated NH4Cl solution and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. LC/MS m/z 267.1 (MH+), Rt 1.47 minutes.

Aufarbeitung

  1. customThe mixture was quenched with an aqueous saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-211b82304f9c4f05bf68fa97f91a988a
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756383B2

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