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

HRID 2080710Notes

Reaction equation

HRID 2080710 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 Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (0.78 g) obtained in Example 1-5 was dissolved in methanol (20 ml) and added with 2-imidazole carboxaldehyde (214 mg) and 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 then added with sodium borohydride (217.8 mg). 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 stirred at room temperature for 15 minutes.

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. stirringstirred at room temperature for 15 minutes

Sources & evidence

ORD record
ord-d5eac26f13c84fea85d0442ab9ba663e
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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