Azidotrimethylsilane → [[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine

HRID 18463

Reaction equation

HRID 18463 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[NH:10]1[C:18]2[C:13](=[CH:14][C:15]([CH:19]=O)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.C[Si]([N:25]=[N+:26]=[N-:27])(C)C.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N+:36]#[C-:37])=[CH:31][CH:30]=1>CO>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:36]2[C:37]([CH:19]([NH:9][CH2:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[C:15]3[CH:14]=[C:13]4[C:18](=[CH:17][CH:16]=3)[NH:10][CH:11]=[CH:12]4)=[N:27][N:26]=[N:25]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 78378AzidotrimethylsilaneHCID 787361H-Imidazole-1-propanamineHCID 589040Indole-5-carboxaldehydeHCID 27574091-Chloro-4-(isocyanomethyl)benzene

Product 1

HCID 59345367[[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Imidazol-1-yl-propylamine (1 mmol) and 1H-Indole-5-carbaldehyde (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-f940c1933ff04e1d9ae29bae6ac77221
Source dataset
uspto-grants-2010_06
Patent number
US07741354B2

Linked notes

Loading…