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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1173838Generated: November 2, 2026

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

https://huagongshe.com/reaction/1173838

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantCyclohexanoneHCID 7967—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-aminobutyl)-benzamideHCID 10317717—
SolventMethanolHCID 887—
Product4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-cyclohexylamino-butyl)-benzamideHCID 10253858—

Reaction Steps

The compound (28.8 mg) obtained in Example 3-2 was dissolved in methanol (0.5 ml). The solution was added with cyclohexanone (8.80 μl) and sodium cyanoborohydride (4.40 mg) and then adjusted to approximately pH 5 with acetic acid, followed by stirring at room temperature for 16 hours. After completion of the reaction, the solvent was distilled off. Then, the residue was dissolved in chloroform and washed with a 1 mol/l sodium hydroxide aqueous solution and saturated saline solution, followed by the addition of 1 mol/l hydrochloric acid to extract the objective substance. Subsequently, the aqueous layer was concentrated under reduced pressure and then the residue was purified through a solid-phase extraction column (Bond Elut® C18 (manufactured by Varian Inc.), 200 mg), thereby obtaining hydrochloride (17.6 mg) of the subject compound as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07833991B2
Source datasetuspto-grants-2010_11
ORD IDord-246b8652524b49d78755512200b09034
Source noteuspto-grants-2010_11