Acetic Acid → HCID 21084459, compound

HRID 1173848Notes

Reaction equation

HRID 1173848 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25]N)=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.C=O.[C:31]([BH3-])#[N:32].[Na+].[C:35](O)(=O)C>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:28]=[CH:27][C:18]([C:19]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][N:32]([CH3:31])[CH3:35])=[O:20])=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 103177174-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-aminobutyl)-benzamide

Product 1

HCID 21084459HCID 21084459, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (27.7 mg) obtained in Example 3-2 was dissolved in anhydrous methanol (1.1 ml). Then, the solution was added with a 36% formaldehyde aqueous solution (manufactured by Kanto Kagaku) (0.0160 ml) and sodium cyanoborohydride (13.2 mg) and adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 22 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 magnesium sulfate. The solvent was distilled off and the residue was then treated with hydrochloric acid. Subsequently, the residue was purified through a solid-phase extraction column (Sep-Pack®, tC18, manufactured by Waters Corporation), thereby obtaining hydrochloride (16.4 mg) of the subject compound 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 magnesium sulfate
  6. distillationThe solvent was distilled off
  7. additionthe residue was then treated with hydrochloric acid
  8. customSubsequently, the residue was purified through a solid-phase extraction column (Sep-Pack®, tC18, manufactured by Waters Corporation)

Sources & evidence

ORD record
ord-c4065433937441e9b494b578b48000ce
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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