Hydrochloric Acid → 1-(3-Phenyl-2-chloropyrid-6-ylmethyl)-5-(4-cyanobenzyl)imidazole hydrochloride salt

HRID 363198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363198
C([N:20]1[CH:24]=[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:34]1([C:40]2[C:41]([Cl:48])=[N:42][C:43]([CH2:46]Br)=[CH:44][CH:45]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>C(#N)C.CO>[ClH:48].[C:34]1([C:40]2[C:41]([Cl:48])=[N:42][C:43]([CH2:46][N:22]3[C:23]([CH2:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=4)=[CH:24][N:20]=[CH:21]3)=[CH:44][CH:45]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 158375331-Trityl-4-(4-cyanobenzyl)imidazoleHCID 543404513-Phenyl-2-chloro-6-bromomethylpyridine

Produkt 1

HCID 867537371-(3-Phenyl-2-chloropyrid-6-ylmethyl)-5-(4-cyanobenzyl)imidazole hydrochloride salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To 1-trityl-4-(4-Cyanobenzyl)-imidazole (88.4 mg, 0.208 mmol) in acetonitrile (1 mL) was added 3-phenyl-2-chloro-6-bromomethylpyridine (53.5 mg, 0.189 mmol) and the mixture heated at 65° C. for 16 hours. The residue was dissolved in methanol (3 ml) and heated at reflux for 2 hours, cooled and evaporated to dryness. The residue was partitioned between sat. aq. Na2CO3 solution and CH2Cl2. The organic layer was dried, (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 2.5-3% MeOH in CH2Cl2) to afford the free base which was converted to the HCl salt by treatment with one equivalent of HCl in aqueous acetonitrile. Evaporation of solvent in vacuo afforded the title compound as a white powder.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. customevaporated to dryness
  5. customThe residue was partitioned between sat. aq. Na2CO3 solution and CH2Cl2
  6. customThe organic layer was dried
  7. custom(MgSO4) and the solvent evaporated in vacuo
  8. customThe residue was chromatographed (Silica gel, 2.5-3% MeOH in CH2Cl2)
  9. customto afford the free base which
  10. customEvaporation of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fac46232c01e4bd9a1edbc7d191fcc30
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872136

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