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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 348594Generated: October 30, 2026

Dicyclohexylcarbodiimide → 4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminophenyl)-benzamide

https://huagongshe.com/reaction/348594

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDicyclohexylcarbodiimideHCID 10868—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantN,N-dipropyl-N'-Boc-1,4-phenylenediamineHCID 23079266—
Reactant4-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic AcidHCID 66941911—
SolventDimethylformamideHCID 6228—
Product4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminophenyl)-benzamideHCID 10051077—

Reaction Steps

The compound (300 mg) obtained in Example 2-2 was dissolved in DMF (10 ml) and added with DCC (298 mg), HOBt (195 mg), and the compound (185 mg) obtained in Example 15-1, followed by stirring overnight at room temperature. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by separating the solution into layers by the addition of 1 mol/l hydrochloric acid. The aqueous layer was made basic by the addition of a 1 mol/l sodium hydroxide aqueous solution. Then, the solution was subjected to extraction with chloroform. The extract was washed with saturated saline solution and the organic layer was then dried with anhydrous sodium sulfate. The solvent was distilled off. Subsequently, the residue was treated with hydrochloric acid and then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (96.4 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-0e57c406745b4e63bc983f31070a5cb5
Source noteuspto-grants-2007_02