1H-imidazole-2-carbaldehyde → (4-dipropylaminobutyl)-(4-{[(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)carbamic Acid t-butyl Ester

HRID 348670Notes

Reaction equation

HRID 348670 reaction equation
[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[NH:29]1[CH:33]=[CH:32][N:31]=[C:30]1[CH:34]=O>CO>[C:1]([O:5][C:6](=[O:28])[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH3:15])[CH2:16][CH2:17][CH3:18])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][NH:27][CH2:34][C:30]2[NH:29][CH:33]=[CH:32][N:31]=2)=[CH:24][CH:25]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 249551H-imidazole-2-carbaldehydeHCID 66941409(4-aminomethylbenzyl)-(4-dipropylaminobutyl)carbamic Acid t-butyl Ester

Product 1

HCID 66941456(4-dipropylaminobutyl)-(4-{[(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)carbamic Acid t-butyl EsterYield 107.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (0.78 g) obtained in Example 25-4 was dissolved in methanol (20 ml) and added with 2-imidazole carboxaldehyde (214.6 mg), followed by stirring at room temperature for 17 hours. After the solvent had been distilled off, the residue was dried under vacuum and then dissolved in methanol (15 ml) and then added with sodium borohydride (217.8 mg), followed by stirring at room temperature for 45 minutes. The reaction solution was added with a saturated aqueous ammonium chloride solution (10 ml) and stirred at room temperature for 15 minutes. Then, the reaction solution was added with saturated saline solution and extracted with chloroform, followed by drying with anhydrous sodium sulfate. After the solvent had been distilled off, the residue obtained was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (1.01 g) as a yellow solid.

Workup

  1. distillationAfter the solvent had been distilled off
  2. customthe residue was dried under vacuum
  3. dissolutiondissolved in methanol (15 ml)
  4. additionadded with sodium borohydride (217.8 mg)
  5. stirringby stirring at room temperature for 45 minutes
  6. additionThe reaction solution was added with a saturated aqueous ammonium chloride solution (10 ml)
  7. stirringstirred at room temperature for 15 minutes
  8. additionThen, the reaction solution was added with saturated saline solution
  9. extractionextracted with chloroform
  10. dry with materialby drying with anhydrous sodium sulfate
  11. distillationAfter the solvent had been distilled off
  12. customthe residue obtained
  13. customwas purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-ed6ecaad2332453286c9b2c01a3f55f3
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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