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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 348651Generated: October 26, 2026

Sodium Hydroxide → N-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(3-methylpyridin-2-ylmethyl)-amino]-methyl}-benzamide

https://huagongshe.com/reaction/348651

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
Reactant3-Methylpyridine-2-carboxaldehydeHCID 1501874—
ReactantSodium cyanoborohydrideHCID 5003444—
ReactantN-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamideHCID 21084514—
SolventAcetic AcidHCID 176—
SolventMethanolHCID 887—
ProductN-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(3-methylpyridin-2-ylmethyl)-amino]-methyl}-benzamideHCID 11756577—

Reaction Steps

The compound (104.9 mg) obtained in Example 47-3 was dissolved in methanol (3.2 ml) and then added with the compound (36.3 mg) obtained in Example 53-1 and sodium cyanoborohydride (31.4 mg). Then, the solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 14 hours. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added to the reaction solution, followed by separation/extraction with chloroform. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and then treated with hydrochloric acid, thereby obtaining hydrochloride (91.5 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-4ad15614b3db4681a9d8210ad8179755
Source noteuspto-grants-2007_02