Imidazole → HCID 68678482, compound

HRID 968633Notes

Reaction equation

HRID 968633 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C[O-].[Na+].[C:9]([O:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C)C=O>[C:9]([O:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10942334Sodium MethoxideHCID 16211353tert-Butyl (6-bromohexyl)carbamate

Product 1

HCID 68678482HCID 68678482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Imidazole (70 mg) and 1.4 M sodium methoxide (1 ml) were added to N,N-dimethylformamide (3 ml) and the mixture was stirred at room temperature for 30 minutes. A solution of N-(tert-butoxycarbonyl)-6-bromo-hexylamine (280 mg) in N,N-dimethylformamide (1 ml) was added and after heating at 80-90° C. for 30 minutes stirring was continued overnight at room temperature. Evaporation in vacuo followed by stirring with acetone and fitration gave a filtrate which after evaporation was purified by chromatography on silica gel with ethyl acetate/methanol (4:1) as eluent to yield the title compound as a colourless oil.

Workup

  1. temperatureafter heating at 80-90° C. for 30 minutes
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. customEvaporation in vacuo
  5. stirringby stirring with acetone and fitration
  6. customgave a filtrate which
  7. customafter evaporation
  8. customwas purified by chromatography on silica gel with ethyl acetate/methanol (4:1) as eluent

Sources & evidence

ORD record
ord-0dd35632519e4527ba18307185074008
Source dataset
uspto-grants-2007_12
Patent number
US07304066B2

Reaction notes

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