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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 240143Generated: October 30, 2026

Diisopropylethylamine → 8-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid [3-(6-dimethylamino-pyridin-3-yl)-phenyl]-amide

https://huagongshe.com/reaction/240143

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant8-Hydroxy-3-carboxy-coumarinHCID 7245716—
ReactantMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Reactant3-(6-Dimethylamino-pyridin-3-yl)-phenylamineHCID 66865517—
SolventDimethylformamideHCID 6228—
Product8-Hydroxy-2-oxo-2H-chromene-3-carboxylic acid [3-(6-dimethylamino-pyridin-3-yl)-phenyl]-amideHCID 8665043342.2%

Reaction Steps

DIEA (0.012 mL, 0.071 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.013 g, 0.065 mmol) and HATU (0.027 g, 0.071 mmol) in 0.5 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(6-dimethylamino-pyridin-3-yl)-phenylamine (0.014 g, 0.065 mmol) was added and allowed to react overnight when a solid precipitated out of solution. The resulting precipitate was filtered, dried under suction, and finally dried overnight in vacuo to give 0.011 g of product in 42% yield: LCMS (ESI) m/z 402 (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08642788B2
Source datasetuspto-grants-2014_02
ORD IDord-bed1ccf0705c4a36869f418796313c30
Source noteuspto-grants-2014_02