Acetic Acid → N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(4-methyl-1H-imidazol-5-ylmethyl)-amino]-methyl}-benzamide

HRID 348616

Reaction equation

HRID 348616 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:28]=[CH:27][CH:26]=[CH:25][C:10]=1C(NCCCCN(CCC)CCC)=O.C([O:34][CH3:35])(OC)OC.[CH3:36][C:37]1[N:38]=[CH:39][NH:40][C:41]=1[CH:42]=O.[C:44]([BH3-])#[N:45].[Na+].[C:48](O)(=O)[CH3:49]>CO>[CH2:26]([N:45]([CH2:44][CH2:48][CH3:49])[CH2:25][CH2:10][CH2:9][CH2:8][NH:7][C:35](=[O:34])[C:26]1[CH:25]=[CH:10][C:9]([CH2:8][N:7]([CH2:6][C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH2:36][C:37]2[NH:38][CH:39]=[N:40][C:41]=2[CH3:42])=[CH:28][CH:27]=1)[CH2:27][CH3:28]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 27958875-Methyl-1H-imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86599830HCID 86599830, compound

Product 1

HCID 178457213N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(4-methyl-1H-imidazol-5-ylmethyl)-amino]-methyl}-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (53.8 mg) obtained in Example 1-4 was dissolved in methanol (0.8 ml). Then, the solution was added with trimethyl orthoformate (50 μl), acetic acid (50 μl), and 4-methyl-5-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (28.5 mg) and stirred at room temperature for 10 minutes. Subsequently, sodium cyanoborohydride (24.4 mg) was added, followed by stirring overnight at room temperature. The solvent was distilled off under reduced pressure and then the residue was dissolved in chloroform, followed by washing with 1 mol/l sodium hydroxide and saturated saline solution and drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (33.5 mg) of the subject compound as a white solid.

Workup

  1. stirringby stirring overnight at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washby washing with 1 mol/l sodium hydroxide and saturated saline solution
  5. dry with materialdrying with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
  9. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-72da7cd121a54b06b2959db25439e293
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Linked notes

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