Acrolein dimer → {(3,4-Dihydro-2H-pyran-2-yl)-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-yl]-methyl}-(3-imidazol-1-yl-propyl)-amine

HRID 18465

Reaction equation

HRID 18465 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH:11]1[CH:16]=O.C[Si]([N:22]=[N+:23]=[N-:24])(C)C.[N+:25]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])#[C-:26]>CO>[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH:11]1[CH:16]([NH:9][CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:26]1[N:25]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[N:24]=[N:23][N:22]=1

Participants

6

Reactant 4

HCID 60994Acrolein dimerHCID 78378AzidotrimethylsilaneHCID 787361H-Imidazole-1-propanamineHCID 27715502-Isocyano-N,N-dimethylethanamine

Product 1

HCID 25059390{(3,4-Dihydro-2H-pyran-2-yl)-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-yl]-methyl}-(3-imidazol-1-yl-propyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Imidazol-1-yl-propylamine (1 mmol) and 3,4-Dihydro-2H-pyran-2-carbaldehyde (1 mmol) were combined in methanol (2 ml, dry). After 2 hours Trimethylsilylazide (5 mmol) and (2-Isocyano-ethyl)-dimethyl-amine (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-859a5691f5d641a8b6aba2247b719733
Source dataset
uspto-grants-2010_06
Patent number
US07741354B2

Linked notes

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