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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1847066Generated: November 1, 2026

Ethanol → 6-[(4R)-4-{[(2S)-2-Hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl]amino}-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

https://huagongshe.com/reaction/1847066

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
Reactanttert-Butyl [(3R)-5-oxopyrrolidin-3-yl]carbamateHCID 71301758—
Reactant6-(Methyloxy)-4-{2-[(2S)-2-oxiranyl]ethyl}pyrido[2,3-b]pyrazin-3(4H)-oneHCID 86649710—
Reactant6-[(4R)-4-amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneHCID 86724991—
SolventWaterHCID 962—
Product6-[(4R)-4-{[(2S)-2-Hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl]amino}-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-oneHCID 60161911—

Reaction Conditions

Temperature80 °C

Reaction Steps

In a mixed solvent (12 ml) of ethanol and water (9:1) were suspended 6-methoxy-4-{2-[(2S)-oxiran-2-yl]ethyl}pyrido[2,3-b]pyrazin-3(4H)-one (290 mg, 1.17 mmol) and 6-[(4R)-4-amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (which was synthesized in the same manner as those of Reference Examples 20, 21 and 22, using the [(3R)-5-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester synthesized with reference to WO2004/22536; 291 mg, 1.17 mmol). The obtained mixture was stirred in a sealed tube at 80° C. for 16 hours.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952010B2
Source datasetuspto-grants-2015_02
ORD IDord-4d9c9b9984ac4a7899437845f1f57787
Source noteuspto-grants-2015_02