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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 68472Generated: October 29, 2026

Acetonitrile → 5-Chloro-N-({3-[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide

https://huagongshe.com/reaction/68472

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetonitrileHCID 6342—
Reactant2-DimethylaminopyridineHCID 21885—
ReactantCarbonylimidazoleHCID 13571086—
Reactant5-Chloro-N-(3-{[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]amino}-2-hydroxypropyl)-2-thiophenecarboxamideHCID 21070710—
Solvent1,4-DioxaneHCID 31275—
Product5-Chloro-N-({3-[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamideHCID 21070709—

Reaction Conditions

Temperature180 °C

Reaction Steps

260 mg (0.608 mmol) of 5-chloro-N-(3-{[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]-amino}-2-hydroxypropyl)-2-thiophenecarboxamide (from Example 61), 197 mg (1.22 mmol) of carbonylimidazole and: 7 mg of dimethylaminopyridine in 20 ml of dioxane are boiled under reflux for 5 hours. 20 ml of acetonitrile are then added, and the mixture is stirred in a closed vessel in a microwave oven at 180° C. for 30 minutes. The solution is concentrated using a rotary evaporator and chromatographed on an RP-HPLC column. This gives 53 mg (19% of theory) of the target compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822458B2
Source datasetuspto-grants-2014_09
ORD IDord-b0dc03a3621541e8a345cb65c8b3b798
Source noteuspto-grants-2014_09