Cesium carbonate → 4-Imidazol-1-ylmethyl-2-[2-(2-oxo-piperidin-1-yl)-phenoxy]-benzonitrile

HRID 1594846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594846
F[C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:16]=[C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:11]1([CH2:10][C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([O:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][C:17]3=[O:16])[CH:9]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 115066091-(2-Hydroxyphenyl)piperidin-2-oneHCID 21697068Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-

Produkt 1

HCID 97996074-Imidazol-1-ylmethyl-2-[2-(2-oxo-piperidin-1-yl)-phenoxy]-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2-Fluoro-4-imidazol-1-ylmethyl-benzonitrile (as described in Step E above) (0.080 g, 0.4 mmol), 2-(2-oxo-piperidin-1-yl)-phenol (as described in Step F above) (0.091 g, 0.5 mmol) and cesium carbonate (0.261 g, 0.8 mmol) were combined in DMF (2.0 mL) and heated at 50° C. for 18 hr. The reaction mixture was partitioned between EtOAc and a minimum volume of H2O. Additional product was salted out from the aqueous layer with solid NaCl, and extracted into EtOAc. The organic layers were combined, dried (Na2SO4), filtered and concentrated to give the title compound after RP HPLC on a Waters Prep Pak column eluting with a 0.1% TFA/H2O: 0.1% TFA/CH3CN gradient followed by conversion to the free base.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc
  2. extractionextracted into EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-764d005d84154974a976aba09e644e7d
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284755B1

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