Azidotrimethylsilane → 2-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol

HRID 18467

Reaction equation

HRID 18467 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:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[C:18]([CH:21]=O)[CH:17]=[CH:16]2.C[Si]([N:27]=[N+:28]=[N-:29])(C)C.[N+:30]([CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])#[C-:31]>CO>[CH3:34][C:33]([CH3:36])([CH3:35])[CH2:32][N:30]1[C:31]([CH:21]([NH:9][CH2:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[C:11]([OH:10])[CH:12]=[CH:13][CH:14]=3)[N:19]=2)=[N:29][N:28]=[N:27]1

Participants

6

Reactant 4

HCID 78378AzidotrimethylsilaneHCID 787361H-Imidazole-1-propanamineHCID 5993428-Hydroxy-2-quinolinecarboxaldehydeHCID 27586461-Isocyano-2,2-dimethyl-propane

Product 1

HCID 250606942-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Imidazol-1-yl-propylamine (1 mmol) and 8-Hydroxy-quinoline-2-carbaldehyde (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-3470187e804f4bbabac598a8116168a6
Source dataset
uspto-grants-2010_06
Patent number
US07741354B2

Linked notes

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