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Acrolein dimer → [(1-Cyclopentyl-1H-tetrazol-5-yl)-(3,4-dihydro-2H-pyran-2-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine

HRID 18464
Notes
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Reaction equation

HRID 18464 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]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)#[C-:26]>CO>[CH:27]1([N:25]2[C:26]([CH:16]([NH:9][CH2:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:11]3[CH2:12][CH2:13][CH:14]=[CH:15][O:10]3)=[N:24][N:23]=[N:22]2)[CH2:31][CH2:30][CH2:29][CH2:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 60994Acrolein dimerHCID 78378AzidotrimethylsilaneHCID 787361H-Imidazole-1-propanamineHCID 2734784Cyclopentyl Isocyanide

Product 1

HCID 25059135[(1-Cyclopentyl-1H-tetrazol-5-yl)-(3,4-dihydro-2H-pyran-2-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

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 Isocyano-cyclopentan (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-3e0f9a51eab2438f8ca1618be1899848
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741354B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes