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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 348588Generated: October 26, 2026

2-Methoxybenzaldehyde → 4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-[4-(2-methoxy-benzylamino)-butyl]-benzamide

https://huagongshe.com/reaction/348588

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-MethoxybenzaldehydeHCID 8658—
ReactantTrimethyl orthoformateHCID 9005—
ReactantSodium borohydrideHCID 4311764—
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-(2-methoxy-benzylamino)-butyl]-benzamideHCID 21084454—

Reaction Steps

The compound (63.9 mg) obtained in Example 3-2 was dissolved in anhydrous methanol (1.3 ml) and then added with 2-methoxybenzaldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (0.0350 ml) and trimethyl orthoformate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (0.0560 ml), followed by stirring at room temperature for 30 minutes. The solution was added with sodium borohydride (19.3 mg), followed by stirring at room temperature for 15 minutes. After completion of the reaction, the solvent was distilled off. Then, the residue was added with water and extracted with chloroform, and the extract was washed with saturated saline solution, followed by drying with anhydrous magnesium sulfate. The solvent was distilled off and treated with hydrochloric acid. The residue was purified through a solid-phase extraction column (Sep-Pack®, tC18, manufactured by Waters Corporation), thereby obtaining hydrochloride (6.80 mg) of the subject compound as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07176227B2
Source datasetuspto-grants-2007_02
ORD IDord-fa404a7480fc461285bb760b9ff59c2b
Source noteuspto-grants-2007_02