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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1695050Generated: October 31, 2026

Triethylamine → (z)-n-(2-Amino-4-chlorophenyl)-6-(2-(2-((5-fluoro-2-oxoindolin-3-ylidene)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamide

https://huagongshe.com/reaction/1695050

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
ReactantSunitinib acidHCID 10979489—
ReactantN-(2-amino-4-chlorophenyl)-6-(2-aminoethylamino)nicotinamideHCID 57993741—
ReactantHCID 178418300HCID 178418300—
SolventDimethylformamideHCID 6228—
SolventSodium chloride; waterHCID 57417360—
Product(z)-n-(2-Amino-4-chlorophenyl)-6-(2-(2-((5-fluoro-2-oxoindolin-3-ylidene)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamideHCID 4453855876%

Reaction Steps

5-(5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (300 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and N-(2-amino-4-chlorophenyl)-6-(2-aminoethylamino)nicotinamide (321 mg, 1.05 mmol) were added. The mixture was stirred for 20 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 (446 mg, 76%) as a yellow solid. LC-MS (m/z) 588 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158656B2
Source datasetuspto-grants-2012_04
ORD IDord-4e1d34f76f74478ab4f16b792466f8c8
Source noteuspto-grants-2012_04