HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1944922Generated: October 30, 2026
Diisopropylethylamine → (R)-N-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)(methyl)amino)pent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide
https://huagongshe.com/reaction/1944922
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-(4(5-bromopent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide | HCID 56923688 | — |
| Reactant | (R)-5-(1-((tert-butyldimethylsilyl)oxy)-2-(methylamino)ethyl)-8-hydroxyquinolin-2(1H)-one | HCID 66988438 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (R)-N-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)(methyl)amino)pent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide | HCID 58505093 | — |
Reaction Steps
A mixture of Intermediate 40 (0.30 g, 0.90 mmol) and Intermediate 4 (375 mg, 1.1 mmol) in DMF (5 mL) was treated with N,N-diisopropylethylamine (0.47 mL, 2.7 mmol) and catalytic tetra-n-butylammonium iodide (100 mg). The mixture was heated for 3 days in a 55° C. oil bath. The mixture was concentrated under reduced pressure and purified via automated flash silica gel chromatography, using a 12 g Silicycle SiliSep flash column (dichloromethane/methanol/ammonium hydroxide). Concentration of the desired fractions under reduced pressure provided the title compound. ES/MS calcd. for C31H39F3N3O4Si+ 602.3. Found m/z=602.4 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394829B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-8a67a7e4f8a84bc58d5953bf0a6e0ceb |
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| Source note | uspto-grants-2013_03 |
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