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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1696224Generated: November 2, 2026

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide

https://huagongshe.com/reaction/1696224

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
ReactantAmmonium ChlorideHCID 25517—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acidHCID 67277241—
SolventWaterHCID 962—
SolventChloroformHCID 6212—
SolventDimethylformamideHCID 6228—
Product4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamideHCID 6727819660.2%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (5.0 mg) in N,N-dimethylformamide (0.1 mL) were added 1-hydroxybenzotriazole (3.9 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (4.5 mg). The mixture was stirred at 60° C. for 30 minutes. To the solution was added ammonium chloride and the mixture was stirred at ambient temperature for 18 hours. To the solution were added water and chloroform and the mixture was extracted with chloroform. The extract was dried over MgSO4, filtrated and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (3 mg) as a white powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163767B2
Source datasetuspto-grants-2012_04
ORD IDord-ef513ab71fd34a67ae1855dee4a2c52c
Source noteuspto-grants-2012_04