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

HRID 18468
Notes
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Reaction equation

HRID 18468 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.[N+:27]([CH:29]1[CH2:31][CH2:30]1)#[C-:28]>CO>[CH:29]1([N:27]2[C:28]([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)[CH2:31][CH2:30]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 78378AzidotrimethylsilaneHCID 787361H-Imidazole-1-propanamineHCID 2758008Isocyanocyclopropane

Product 1

HCID 250606982-[(1-Cyclopropyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

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 Isocyano-cyclopropane (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-e00c3fef56994855928f8ddb1e1bebb6
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