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

HRID 18462

Reaction equation

HRID 18462 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.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][N+:35]#[C-:36])=[CH:30][CH:29]=1>CO>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][N:35]2[C:36]([CH:13]([NH:9][CH2:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[C:12]3[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:11]=3[OH:10])=[N:26][N:25]=[N:24]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 78378AzidotrimethylsilaneHCID 787361H-Imidazole-1-propanamineHCID 27574091-Chloro-4-(isocyanomethyl)benzene

Product 1

HCID 250622412-[[1-(4-Chloro-benzyl)-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-Chloro-4-isocyanomethyl-benzene (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-9eb22706214142e0979a67926478b28b
Source dataset
uspto-grants-2010_06
Patent number
US07741354B2

Linked notes

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