3-Aminopyridine-2-carbonitrile → HCID 178480640, Verbindung

HRID 353800

Reaktionsgleichung

Reaktionsgleichung von HRID 353800
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:32]=[CH:31][C:21]3[NH:22][C:23]([CH2:25][C:26]([O:28]CC)=O)=[N:24][C:20]=3[CH:19]=2)[CH2:14][CH2:13]1.[NH2:33][C:34]1[C:35]([C:40]#[N:41])=[N:36][CH:37]=[CH:38][CH:39]=1>C1COCC1>[NH2:41][C:40]1[C:35]2[C:34](=[CH:39][CH:38]=[CH:37][N:36]=2)[NH:33][C:26](=[O:28])[C:25]=1[C:23]1[NH:22][C:21]2[CH:31]=[CH:32][C:18]([N:15]3[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH2:16]3)=[CH:19][C:20]=2[N:24]=1

Komponenten

5

Edukt 3

HCID 5770153-Aminopyridine-2-carbonitrileHCID 2733832Lithium HexamethyldisilazideHCID 178470776HCID 178470776, Verbindung

Produkt 1

HCID 178480640HCID 178480640, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

LiHMDS (3.6 eq) was added to ethyl [5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetate (1.0 eq) and 3-aminopyridine-2-carbonitrile (1.0 eq) in THF at 0° C. The reaction was stirred overnight and then heated at 40° C. for 3 hours. The resulting mixture was quenched with an aqueous saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a green solid. The crude material was washed successively with CH2Cl2 and MeOH, and then was purified by reverse phase HPLC to provide the desired product. LC/MS m/z 376.1 (MH+), Rt 1.50 minutes.

Aufarbeitung

  1. customThe resulting mixture was quenched with an aqueous saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a green solid
  8. washThe crude material was washed successively with CH2Cl2 and MeOH
  9. customwas purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0e37607eee534c6a88a584b2dd4318da
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756383B2

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