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Chemical Structure| 835616-61-0 Chemical Structure| 835616-61-0
Chemical Structure| 835616-61-0

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Thalidomide 5-fluoride is a Thalidomide-based cereblon ligand that conjugates with an IRAK4 protein ligand via a linker to form a PROTAC IRAK4 degrader.

4.5 *For Research Use Only !

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Product Details of Thalidomide 5-fluoride

CAS No. :835616-61-0
Formula : C13H9FN2O4
M.W : 276.22
SMILES Code : O=C1N(C(CC2)C(NC2=O)=O)C(C3=C1C=CC(F)=C3)=O
MDL No. :MFCD30188075
InChI Key :MPQLCQKBYRSPNA-UHFFFAOYSA-N
Pubchem ID :70876201

Safety of Thalidomide 5-fluoride

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of Thalidomide 5-fluoride

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 835616-61-0 ]

[ 835616-61-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 835616-61-0 ]
  • [ 131922-05-9 ]
  • C18H17F3N4O4 [ No CAS ]
  • 2
  • [ 835616-61-0 ]
  • [ 131922-05-9 ]
  • 2-(2,6-dioxopiperidin-3-yl)-5-(4-(6-((1r,3r)-3-((5-(5-methyl-5H-pyrido[4,3-b]indol-7-yl)pyridin-2-yl)oxy)cyclobutoxy)hexyl)-3-(trifluoromethyl)piperazin-1-yl)isoindoline-1,3-dione [ No CAS ]
  • 3
  • [ 845305-83-1 ]
  • [ 835616-61-0 ]
  • tert-butyl 4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)oxy)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92.6% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 2h;Sealed tube; Into a 30-mL sealed tube, was placed tert-butyl 4-(piperidin-4-yloxy)piperidine-1- carboxylate (500 mg, 1.7 mmol, 1.0 equiv), 2-(2,6-dioxopiperidin-3-yl)-5-fluoroisoindole-1,3- dione (509.9 mg, 1.8 mmol, 1.05 equiv), DIEA (681.7 mg, 5.3mmol, 3.0 equiv) in DMF (20 mL). The resulting mixture was stirred for 2 hours at 100 C in an oil bath. Then the mixture was diluted with 20 mL of water and extracted with ethyl acetate (20 mL x 2). The organic layers were combined and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (2:1). This resulted in 880 mg (92.6%) of tert-butyl 4-([1-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl]piperidin-4- yl]oxy)piperidine-1-carboxylate as a yellow solid. LC/MS (ESI) m/z: 541.35 [M+1] +.
 

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