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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1693461Generated: November 2, 2026

Propylamine → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(R)-hydroxy-2-propylcarbamoylethyl)amide

https://huagongshe.com/reaction/1693461

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPropylamineHCID 7852—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantDiisopropylethylamineHCID 81531—
Reactant(S)-3-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-(R)-2-hydroxy-4-phenylbutyric acidHCID 59753553—
SolventDimethylformamideHCID 6228—
Product5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-benzyl-2-(R)-hydroxy-2-propylcarbamoylethyl)amideHCID 59753595—

Reaction Steps

n-Propylamine (16 μL, 0.19 mmol) was added to a solution of 3-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-2-(R)-hydroxy-4-phenylbutyric acid (EXAMPLE 44, 40 mg, 0.11 mmol), HOBt (16.4 mg, 0.11 mmol), DIPEA (41 μL, 0.24 mmol) and EDCI (25 mg, 0.13 mmol) in DMF (3 mL). After stirring for 72 h at room temperature the solvent was removed in vacuo and the remaining residue was purified by preparative LCMS to give the title compound as colourless solid. m/z (ES+)=415.34 [M+H]+; RT=3.10 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158622B2
Source datasetuspto-grants-2012_04
ORD IDord-7755e580c9764a70a03e3a29b0e7d467
Source noteuspto-grants-2012_04