Sodium Hydroxide → (4-{[bis(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylaminomethylphenyl)-amine

HRID 348635Notes

Reaction equation

HRID 348635 reaction equation
[NH2:1][CH2:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH:31]=O.[C:33]([BH3-])#[N:34].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH3:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH2:31][N:1]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[CH:11][CH:10]=2)=[CH:23][CH:24]=1)[CH2:10][C:9]1[N:34]([CH3:33])[CH:6]=[CH:7][N:8]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23079293(4-Aminomethylbenzyl)-(4-dipropylaminomethylphenyl)-amine

Product 1

HCID 58801914(4-{[bis(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(4-dipropylaminomethylphenyl)-amineYield 122.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The compound (57.3 mg) obtained in Example 39-2 was dissolved in methanol (2.5 ml). The solution was added with 1-methyl-2-imidazole carboxaldehyde (158 mg) and then added with sodium cyanoborohydride (68.4 mg). The reaction solution was adjusted to pH 5 by the addition of acetic acid, followed by stirring for 17 hours at room temperature. Then, the reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. After that, the organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. After the solvent had been distilled off, a 10% hydrogen chloride/methanol solution was added to the residue, and the solvent was then distilled off. The residue obtained was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (55.2 mg) as a yellow solid.

Workup

  1. extractionsubjected to extraction with chloroform
  2. washAfter that, the organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationAfter the solvent had been distilled off
  5. additiona 10% hydrogen chloride/methanol solution was added to the residue
  6. distillationthe solvent was then distilled off
  7. customThe residue obtained
  8. customwas purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-0d1f158ecc154a12bc1e9337dbb4b01e
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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