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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1987887Generated: November 4, 2026

1,2-Dichloroethane → 4-(4-chlorophenyl)-N-(3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-1H-pyrrole-2-carboxamide

https://huagongshe.com/reaction/1987887

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantSodium BicarbonateHCID 516892—
Reactant3-Methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)anilineHCID 11736503—
Reactant4-(4-Chlorophenyl)-1H-pyrrole-2-carboxylic acidHCID 12897099—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product4-(4-chlorophenyl)-N-(3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-1H-pyrrole-2-carboxamideHCID 6721558499%

Reaction Steps

Following preparation as described in Patent: WO2002/101146, 3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)benzenamine (59 mg, 0.25 mol) was stirred overnight in DMF (2 mL) containing with 4-(4-chlorophenyl)-1H-pyrrole-2-carboxylic acid (65 mg, 0.25 mol), EDC (96 mg, 0.50 mol), HOBT (77 mg, 0.50 mol) and NaHCO3 (116 mg, 1.37 mol). After dilution of the reaction with 40 mL of EtOAc, the organic layer was washed with H2O (10 mL×2) and brine. The organic layer was dried over Na2SO4, and conc. in vacuum to a brown oil. The oil was purified by flash column chromatography (silica gel, CH3OH in CH2Cl2, 0-10% gradient) to yield 109 mg (99%) of the title compound as a colorless oil. MS (ESI) 440 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07553836B2
Source datasetuspto-grants-2009_06
ORD IDord-04ffb41c291b445f94ea5d25b05d44ee
Source noteuspto-grants-2009_06