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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 348601Generated: October 29, 2026

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

https://huagongshe.com/reaction/348601

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant2-PyridinecarboxaldehydeHCID 14273—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant4-{[N-Boc-N-(1H-imidazol-2-ylmethyl)amino]methyl}-N-(4-dipropylaminobutyl)benzamideHCID 21084475—
SolventMethanolHCID 887—
ProductN-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-pyridin-2-ylmethylamino]-methyl}-benzamideHCID 10457708—

Reaction Steps

The compound (39.8 mg) obtained in Example 1-3 and pyridine-2-aldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (16.1 mg) were dissolved in anhydrous methanol (2.0 ml). The solution was added with sodium cyanoborohydride (18.9 mg) and then adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 39.5 hours. After completion of the reaction, the solvent was distilled off. The residue was dissolved in chloroform and then washed with a 1 mol/l sodium hydroxide and saturated saline solution, followed by drying with anhydrous magnesium sulfate. Subsequently, the residue was distilled off and the residue was then treated with hydrochloric acid. The residue was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (7.00 mg) of the subject compound as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07176227B2
Source datasetuspto-grants-2007_02
ORD IDord-8e26adee2ed54e4cad9e6d3d6a04e627
Source noteuspto-grants-2007_02