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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 348637Generated: October 27, 2026

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

https://huagongshe.com/reaction/348637

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDicyclohexylcarbodiimideHCID 10868—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantN,N-dipropylbutane-1,4-diamineHCID 7138396—
Reactant4-{[bis(1-methyl-1H-imidazol-2-ylmethyl)amino]methyl}-benzoic AcidHCID 66941805—
SolventDimethylformamideHCID 6228—
Product4-{[bis(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(4-dipropylaminobutyl)-benzamideHCID 58801911—

Reaction Steps

The compound (75.0 mg) obtained in Example 40-1 was dissolved in DMF (2.0 ml) and then added with DCC (46.0 mg) and HOBt (36.0 mg), followed by stirring for 6 hours. A solution of the compound (76.0 mg) obtained in Example 1-2 in DMF was added to the reaction system and then the whole was stirred for 15 hours. After completion of the reaction, DMF was distilled off and the residue was then dissolved in chloroform, followed by extraction with 1 mol/l hydrochloric acid. The aqueous layer was added with a 1 mol/l sodium hydroxide aqueous solution and then extracted with chloroform. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off, followed by treating with hydrochloric acid. Subsequently, the treated product was purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (23.9 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-03d953a9c8a84e2aa261bd318474ed65
Source noteuspto-grants-2007_02