Ethyl Acetate → 2-Propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrile

HRID 265107Notes

Reaction equation

HRID 265107 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([C:10]1[NH:11][C:12]([C:21]#[N:22])=[C:13]([C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[N:14]=1)[CH2:8][CH3:9].[C:23]([N:42]1[C:46]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[C:53]2[CH:60]=[CH:59][C:56]([CH2:57]Br)=[CH:55][CH:54]=2)=[N:45][N:44]=[N:43]1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C>CN(C)C(=O)C.O>[CH2:7]([C:10]1[N:11]([CH2:57][C:56]2[CH:55]=[CH:54][C:53]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[C:46]3[N:42]([C:23]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:43]=[N:44][N:45]=3)=[CH:60][CH:59]=2)[C:12]([C:21]#[N:22])=[C:13]([C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])[N:14]=1)[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 23665647Potassium tert-butoxideHCID 1784401442-Propyl-4-pivaloylimidazole-5-carbonitrile

Product 1

HCID 217408232-Propyl-4-pivaloyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carbonitrileYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

1.08 g of potassium t-butoxide was added, whilst ice-cooling, to a solution of 2.00 g of 2-propyl-4-pivaloylimidazole-5-carbonitrile (prepared as described in Preparation 41) in 20 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at same temperature for 10 minutes. 6.10 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide were then added to the solution, and the resulting mixture was stirred at 50° C. for 4 hours. At the end of this time, ethyl acetate and water were added to the mixture, and the ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The syrupy residue was purified by column chromatography through silica gel, using 1:3 and 1:2 by volume mixtures of ethyl acetate and hexane as the eluent, to give 5.44 g of the title compound as crystals, melting at 107°-110° C.

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 4 hours
  2. customthe ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe syrupy residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-6391692c71d74f7faaee1bd70f902a05
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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