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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 591915Generated: November 1, 2026

Diisopropylethylamine → (1S,2S,3R,4R)-3-(2-Amino-5-chloro-3-nitro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

https://huagongshe.com/reaction/591915

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant2-Amino-4,5-dichloro-3-nitropyridineHCID 46867660—
Reactant(1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide trifluoroacetic acid saltHCID 67264207—
SolventIsopropanolHCID 3776—
Product(1S,2S,3R,4R)-3-(2-Amino-5-chloro-3-nitro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideHCID 11770194295%

Reaction Conditions

Temperature60 °C

Reaction Steps

4,5-Dichloro-3-nitro-pyridin-2-ylamine (1.01 g, 4.86 mmol) and (1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide trifluoroacetic acid salt (1.5 g, 5.5 mmol) were combined with N,N-diisopropylethylamine (3.3 g, 26 mmol) in isopropanol (15 mL) and heated at 60° C. overnight. The reaction was permitted to cool to room temperature and the orange solid which had formed was isolated by filtration. The solid was washed with 3 mL cold isopropanol and was dried in an air stream to afford 1.493 g (95%) of the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09238656B2
Source datasetuspto-grants-2016_01
ORD IDord-907401a30dbb4a4db2b6256fb1234200
Source noteuspto-grants-2016_01