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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 43182Generated: October 26, 2026

Sodium Bicarbonate → 8-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (5-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-pyridin-2-yl)-amide

https://huagongshe.com/reaction/43182

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantTrimethylaluminumHCID 16682925—
Reactant5-({[2-(Dimethylamino)ethyl](methyl)amino}methyl)pyridin-2-amineHCID 59292945—
Reactant8-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl esterHCID 86641146—
SolventDichloromethaneHCID 6344—
SolventDichloromethane methanolHCID 21226129—
Product8-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (5-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-pyridin-2-yl)-amideHCID 59292954—

Reaction Conditions

Temperature80 °C

Reaction Steps

The title compound was prepared in analogy to the procedure described in Example 115 but using 8-(2-chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 144.1), N-(6-amino-pyridin-3-ylmethyl)-N,N′,N′-trimethyl-ethane-1,2-diamine (prepared as described in Example 26 but using N,N,N′-trimethyl-ethane-1,2-diamine in Step 26.2 and purified by column chromatography), 2 equiv of trimethyl aluminum, stirring the reaction mixture for 5 h at 80° C., pouring it onto a saturated aqueous solution of NaHCO3 and DCM. The title compound: ESI-MS: 553.1 [M+H]+; tR=3.43 min (System 1); TLC: Rf=0.06 (DCM/MeOH/NH3aq, 94:5:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08536175B2
Source datasetuspto-grants-2013_09
ORD IDord-c2fb864ecefa455f8726360ea5cb7d52
Source noteuspto-grants-2013_09