3-Aminopyridine-2-carbonitrile → HCID 178482919, Verbindung

HRID 2221043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221043
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][N:12]([CH3:33])[CH:13]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](OCC)=[O:27])=[N:24][C:20]=3[CH:19]=2)[CH2:14]1.[NH2:34][C:35]1[C:36]([C:41]#[N:42])=[N:37][CH:38]=[CH:39][CH:40]=1>C1COCC1>[NH2:42][C:41]1[C:36]2[C:35](=[CH:40][CH:39]=[CH:38][N:37]=2)[NH:34][C:26](=[O:27])[C:25]=1[C:23]1[NH:22][C:21]2[CH:31]=[CH:32][C:18]([N:15]3[CH2:16][CH2:17][CH:13]([N:12]([CH3:11])[CH3:33])[CH2:14]3)=[CH:19][C:20]=2[N:24]=1

Komponenten

5

Edukt 3

HCID 5770153-Aminopyridine-2-carbonitrileHCID 2733832Lithium HexamethyldisilazideHCID 178470775HCID 178470775, Verbindung

Produkt 1

HCID 178482919HCID 178482919, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

LiHMDS (3.6 eq) was added to ethyl {5-[3-(dimethylamino)pyrrolidin-1-yl]-1H-benzimidazol-2-yl}acetate (1.0 eq) and 3-aminopyridine-2-carbonitrile (J. Org. Chem. 1958, 1616-1617; 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 390.2 (MH+), Rt 1.79 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-7f7bf868039d41939a540730437d577d
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368459B2

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