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

HRID 363198Notes

Reaction equation

HRID 363198 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fac46232c01e4bd9a1edbc7d191fcc30
Source dataset
uspto-grants-1999_02
Patent number
US05872136

Reaction notes

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