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

HRID 2080864Notes

Reaction equation

HRID 2080864 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 76-3 was dissolved in methanol (20 ml) and added with 2-imidazole carboxaldehyde (214.6 mg). The whole was stirred at room temperature for 17 hours. After the solvent was distilled off, the resultant was dried under vacuum, dissolved in methanol (15 ml), and added with sodium borohydride (217.8 mg) and the whole was stirred at room temperature for 45 minutes. The reaction solution was added with a saturated aqueous ammonium chloride solution (10 ml) and the whole was stirred at room temperature for 15 minutes. The reaction solution was added with a saturated saline solution and subjected to extraction with chloroform, followed by drying with anhydrous sodium sulfate. The solvent was distilled off. Then, the resultant residue 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 was distilled off
  2. customthe resultant was dried under vacuum
  3. dissolutiondissolved in methanol (15 ml)
  4. additionadded with sodium borohydride (217.8 mg)
  5. stirringthe whole was stirred at room temperature for 45 minutes
  6. additionThe reaction solution was added with a saturated aqueous ammonium chloride solution (10 ml)
  7. stirringthe whole was stirred at room temperature for 15 minutes
  8. additionThe reaction solution was added with a saturated saline solution
  9. extractionsubjected to extraction with chloroform
  10. dry with materialby drying with anhydrous sodium sulfate
  11. distillationThe solvent was distilled off
  12. customThen, the resultant residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-1ed38c6ab5c945eba88e9ca71c77706e
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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