Acetic Acid → N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(6-methylpyridin-2-yl-methyl)-amino]-methyl}-benzamide

HRID 348643Notes

Reaction equation

HRID 348643 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.[CH3:29][C:30]1[N:35]=[C:34]([CH:36]=O)[CH:33]=[CH:32][CH:31]=1.[C:38]([BH3-])#[N:39].[Na+].[C:42](O)(=O)[CH3:43].[CH3:46][OH:47]>>[CH2:26]([N:39]([CH2:38][CH2:42][CH3:43])[CH2:25][CH2:10][CH2:9][CH2:8][NH:7][C:46](=[O:47])[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)[CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[C:34]([CH3:36])[N:35]=2)=[CH:28][CH:27]=1)[CH2:27][CH3:28]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86599830[N-(1H-imidazol-2-ylmethyl)amino]methyl-N-(4-dipropylaminobutyl)benzamide

Product 1

HCID 10390883N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(6-methylpyridin-2-yl-methyl)-amino]-methyl}-benzamide

Procedure

The compound (44.3 mg) obtained in Example 1-4 was dissolved in methanol (1.0 ml) and then added with 6-methylpyridine-2-carboxaldehyde (20.7 mg) and sodium cyanoborohydride (10.7 mg). The solution was adjusted to about pH 5 with acetic acid and then stirred at room temperature for 15 hours. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by washing with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution and drying with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining the subject compound (9.9 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. washby washing with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution
  5. dry with materialdrying with anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform/methanol/water)

Sources & evidence

ORD record
ord-36297dc20033451e88941f46c629101b
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

Loading…