Acetic Acid → (4-dipropylaminobutyl)-(4-{[(1H-imidazol-2-ylmethyl)-(5-methylpyridin-2-ylmethyl)amino]methyl}benzyl)carbamic Acid t-butyl Ester

HRID 348671Notes

Reaction equation

HRID 348671 reaction equation
[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:35]([BH3-])#[N:36].[Na+].[C:39](O)(=O)[CH3:40].[OH-].[Na+]>CO>[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:23][CH2:24][CH2:25][CH2:26][N:27]([CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH3:33])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH2:17][C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)[CH2:11][C:10]2[CH:9]=[CH:8][C:39]([CH3:40])=[CH:35][N:36]=2)=[CH:13][CH:14]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 66941456(4-dipropylaminobutyl)-(4-{[(1H-imidazol-2-ylmethyl)amino]methyl}benzyl)carbamic Acid t-butyl Ester

Product 1

HCID 66941714(4-dipropylaminobutyl)-(4-{[(1H-imidazol-2-ylmethyl)-(5-methylpyridin-2-ylmethyl)amino]methyl}benzyl)carbamic Acid t-butyl Ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (61.6 mg) obtained in Example 75-1 was dissolved in methanol (2.0 ml) and then added with the compound (23.8 mg) obtained in Example 56-1, followed by the addition of sodium cyanoborohydride (15.8 mg). The reaction solution was added with acetic acid to adjust the solution to pH 5, followed by stirring at room temperature for 17 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and extracted with chloroform. After that, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After the solvent had been distilled off, the residue obtained was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (36.7 mg) as a yellow solid.

Workup

  1. extractionextracted 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. customthe residue obtained
  6. customwas purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-85ff0d2cfcc248f8b1f2e277f0453289
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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