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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1247514Generated: October 30, 2026

Dichloromethane → 2,3-Dichloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-4H-thieno[3,2-b]pyrrole-5-carboxamide

https://huagongshe.com/reaction/1247514

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant2-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 10002061—
Reactant2-chloro-N-[1-(2-hydroxyethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 10430450—
SolventWaterHCID 962—
Product2,3-Dichloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-4H-thieno[3,2-b]pyrrole-5-carboxamideHCID 10479003—

Reaction Steps

5-Carboxy-2,3-dichloro-4H-thieno[3,2-b]pyrrole (Method 8; 595 mg, 2.52 mmol), HOBt (340 mg, 2.52 mmol), DCM (100 mL) and finally EDCI (483 mg, 2.52 mmol) were added to methyl (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate (Method 1, 590 mg, 2.52 mmol) and the reaction was stirred for 18 hours The reaction was then diluted with water (50 mL) and stirred vigorously for 30 min. The resultant precipitate was filtered and washed with Et2O (2×20 mL). After filtration the resultant solid was then triturated with refluxing Et2O (25 mL) and after cooling the title compound (528 mg, 46%) was collected again by filtration as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07129249B2
Source datasetuspto-grants-2006_10
ORD IDord-6b15385fe3a54cf9b51be33c9f69624a
Source noteuspto-grants-2006_10