Benzaldehyde, 2-hydroxy-5-methyl- → 2-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol

HRID 18466

Reaction equation

HRID 18466 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[OH:10][C:11]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:12]=1[CH:13]=O.C[Si]([N:24]=[N+:25]=[N-:26])(C)C.[N+:27]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])#[C-:28]>CO>[CH3:31][C:30]([CH3:33])([CH3:32])[CH2:29][N:27]1[C:28]([CH:13]([NH:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:12]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:11]=2[OH:10])=[N:26][N:25]=[N:24]1

Participants

6

Reactant 4

HCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 78378AzidotrimethylsilaneHCID 787361H-Imidazole-1-propanamineHCID 27586461-Isocyano-2,2-dimethyl-propane

Product 1

HCID 593454072-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Imidazol-1-yl-propylamine (1 mmol) and 2-Hydroxy-5-methyl-benzaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours Trimethylsilylazide (5 mmol) and 1-Isocyano-2,2-dimethyl-propane (1 mmol) was added. The reaction was stirred at room temperature for 48 h. After evaporation of the solvent the residue was purified with chromatographic methods.

Workup

  1. customAfter evaporation of the solvent the residue
  2. customwas purified with chromatographic methods

Sources & evidence

ORD record
ord-cfceddfb4bc9409090c9ad66df42eb23
Source dataset
uspto-grants-2010_06
Patent number
US07741354B2

Linked notes

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