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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 469002Generated: October 26, 2026

Hydrochloric Acid → 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-N-methylfuran-3-carboxamide

https://huagongshe.com/reaction/469002

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantDiisopropylethylamineHCID 81531—
Reactant5-({[(4-Bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acidHCID 58393425—
Reactant2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamineHCID 67217191—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-N-methylfuran-3-carboxamideHCID 46175364—

Reaction Steps

To a stirred solution of 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (54 mg, 0.12 mmol), EDCI (29 mg, 0.15 mmol) and HOBt (20 mg, 0.15 mmol) in DMF (3 mL) was added a solution of 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine.HCl (29 mg, 0.11 mmol) and DIPEA (0.084 mL, 0.48 mmol) in DMF (2 mL). The reaction was stirred at ambient temperature for 18 h, then diluted with EtOAc. The solution was washed with water, saturated aqueous NaHCO3 and 1:1 saturated brine:water. The organic extracts were dried over MgSO4, and solvent was removed in vacuo. A portion of the crude product was purified using prep method C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08623859B2
Source datasetuspto-grants-2014_01
ORD IDord-868d4065189749e38d4558a0ebe7820e
Source noteuspto-grants-2014_01