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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 499338Generated: October 30, 2026

Dimethylformamide → N-(2-Methoxyethyl)-6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxamide

https://huagongshe.com/reaction/499338

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylic acidHCID 22939339—
SolventWaterHCID 962—
ProductN-(2-Methoxyethyl)-6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxamideHCID 5975036940%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylic acid (350 mg, 1.2 mmol), WSC (471 mg, 2.4 mmol), HOBt (332 mg, 2.4 mmol) and DMF (10 ml) was stirred at 80° C. for 17 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-methanol (50:1, v/v) and recrystallized from tetrahydrofuran-hexane to give the titled compound (167 mg, 40%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07767665B2
Source datasetuspto-grants-2010_08
ORD IDord-fd9ff093ff8a45008579c5ac7bb0623b
Source noteuspto-grants-2010_08