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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 897374Generated: October 30, 2026

Acetic Acid → HCID 22346388, compound

https://huagongshe.com/reaction/897374

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantTriethylamineHCID 8471—
ReactantHCID 16753952HCID 16753952—
ReactantMethyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylateHCID 22343006—
SolventEthanolHCID 702—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
ProductHCID 22346388HCID 22346388—

Reaction Conditions

Temperature78 °C

Reaction Steps

A mixture of 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylic acid methyl ester (1.00 g, 3.53 mmol, see Example 113), 2-(aminomethyl)-5-fluoro-N,N-dimethylbenzenesulfonamide (1.64 g, 7.07 mmol), and triethylamine (0.99 mL, 7.07 mmol) in EtOH (8 mL) and DMF (2 mL) was heated to 78° C. overnight. The mixture was cooled to 40° C. and glacial acetic acid (0.81 mL, 14.1 mmol) was added. The mixture was allowed to cool to room temperature and water was added dropwise while sonicating to facilitate the product precipitating out of solution. The solids were collected by vacuum filtration to afford the desired product as a light yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06921759B2
Source datasetuspto-grants-2005_07
ORD IDord-37942bb80a234eb58aab379bf1569272
Source noteuspto-grants-2005_07