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HomeProduct name list2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione

2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione

2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione Structural

What is 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione?

Description

4-Fluoro-thalidomide is the Thalidomide-based Cereblon ligand used in the recruitment of CRBN protein. It can be connected to the ligand for IRAK4 protein by a linker to form PROTAC IRAK4 degrader-1 (HY-129966).

The Uses of 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione

2-(2,6-Dioxo-3-piperidinyl)-4-fluoro-1H-isoindole-1,3(2H)-dione is an intermediate in the synthesis of N-[2-Aminoethyl] Pomalidomide TFA Salt (A6095150. N-[2-Aminoethyl] Pomalidomide TFA is a thalidomide derivative, a potent inhibitor of TNF-α production. It is an anti-inflammatory and anti-tumor agent used in the treatment of multiple myeloma.

Synthesis

A mixture of 4-fluoroisobenzofuran-l,3-dione (498.33 mg, 3.00 mmol), 3- aminopiperidine-2,6-dione hydrogen chloride (493.77 mg, 3.00 mmol) and NaOAc (246.09 mg, 3.00 mmol) in HOAc (10 mL) was stirred at 135 °C overnight, cooled and concentrated in vacuo. The residue was suspended in H2O (100 mL) and stirred at room temperature for 4 hours. The solid was collected via filtration and dried in vacuo to afford 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione as a white solid.
2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione

storage

Store at +4°C

Properties of 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione

Melting point: 254-256°C
Boiling point: 520.9±45.0 °C(Predicted)
Density  1.570±0.06 g/cm3(Predicted)
storage temp.  2-8°C
solubility  Dichloromethane (Slightly, Heated), DMSO (Slightly)
form  Solid
pka 10.63±0.40(Predicted)
color  White to Off-White
InChI InChI=1S/C13H9FN2O4/c14-7-3-1-2-6-10(7)13(20)16(12(6)19)8-4-5-9(17)15-11(8)18/h1-3,8H,4-5H2,(H,15,17,18)

Safety information for 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione

Computed Descriptors for 2-(2,6-dioxopiperidin-3-yl)-4-fluoroisoindoline-1,3-dione

InChIKey CRAUTELYXAAAPW-UHFFFAOYSA-N
SMILES C1(=O)C2=C(C(F)=CC=C2)C(=O)N1C1CCC(=O)NC1=O

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