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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 251655Generated: October 26, 2026

Triethylamine → 2-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-acetic acid methyl ester

https://huagongshe.com/reaction/251655

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantGlycine methyl ester hydrochlorideHCID 122755—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
Reactant5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acidHCID 136387942—
ReactantHCID 178418300HCID 178418300—
SolventDimethylformamideHCID 6228—
SolventSodium chloride; waterHCID 57417360—
Product2-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-acetic acid methyl esterHCID 13638794161.1%

Reaction Steps

5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (328 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxybenzo-triazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and glycine methyl ester hydrochloride (151.8 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (244 mg, 61% yield) as a red solid. LC-MS (m/z) 400 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07863315B2
Source datasetuspto-grants-2011_01
ORD IDord-ab718c68b33e4308a7998e3056c44c39
Source noteuspto-grants-2011_01