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Chemical Structure| 2765625-93-0 Chemical Structure| 2765625-93-0

Structure of SJ6986
CAS No.: 2765625-93-0

Chemical Structure| 2765625-93-0

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Product Details of [ 2765625-93-0 ]

CAS No. :2765625-93-0
Formula : C20H14F3N3O7S
M.W : 497.40
SMILES Code : O=S(C1=CC=CC=C1OC(F)(F)F)(NC2=CC3=C(C(N(C(CC4)C(NC4=O)=O)C3=O)=O)C=C2)=O
English Name :N-(2-(2,6-Dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)-2-(trifluoromethoxy)benzenesulfonamide
MDL No. :N/A
InChI Key :RKAFYSIKAVFVPS-UHFFFAOYSA-N
Pubchem ID :155925914

Safety of [ 2765625-93-0 ]

Application In Synthesis of [ 2765625-93-0 ]

* 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 [ 2765625-93-0 ]

[ 2765625-93-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 191732-76-0 ]
  • [ 103008-51-1 ]
  • [ 2765625-93-0 ]
YieldReaction ConditionsOperation in experiment
68% In pyridine at 80℃; for 16h; Inert atmosphere;
44% With pyridine at 80℃; for 12h; 7.A Step A. Preparation of Compound IG-9 Compound IG-9 A mixture of 5-amino-2-(26-dioxopiperidin-3-yl)isoindoline-1,3-dione (500 mg, 1.83 mmol, 100 eq) and 2-(trifluoromethoxy)benzene-1-sulfonyl chloride (954 mg, 3.66 mmol, 2.00 eq) in pyridine (8 mL) was stirred at 80 °C for 12 h. The mixture was concentrated to give a residue. The residue was purified by Prep-HPLC (column: Phenomenex luna C18 150*25mm*10um; mobile phase: [water(FA)-ACN]; B%: 36%-66%, 10 min) and lyophilized to afford N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)-2-(trifluoromethoxy)benzenesulfonamide, Compound IG-9, (409.01 mg, 814 umol, 44% yield, 99% purity) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 11.60 (s, 1H), 11.10 (s, 1H), 8.10 (dd, J=1.6, 8.0 Hz, 1H), 7.91-7.76 (m, 2H), 7.70-7.56 (m, 2H), 7.55-7.46 (m, 2H), 5.09 (dd, J=5.6, 12.8 Hz, 1H), 2.93-2.80 (m, 1H), 2.60 (br d, J=2.4 Hz, 1H), 2.43 (br d, J=4.4 Hz, 1H), 2.07-1.96 (m, 1H) MS (ESI) m/z 498.2 [M-H]+
With pyridine at 80℃; for 16h; Inert atmosphere; 3 GENERAL PROCEDURE FOR THE SYNTHESIS OF SULFONAMIDES. General procedure: In a 48 position Mettler Toledo XT reaction block containing 11 .5 x 110 mm test tubes equipped with a stir bar was added 0.1 mmol of 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline- 1 , 3-dione and the corresponding sulfonyl chloride (2.0 equiv, 0.2 mmol) for compounds 1-37 and 94-103, whereas 0.075 mmol of 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1 , 3-dione and the corresponding sulfonyl chloride (2.0 equiv, 0.15 mmol) for compounds 38-93 (see Table 2 immediately following the Examples below). Anhydrous pyridine (500 uL) was added and the reactions were heated in a reaction block to 80 °C and stirred overnight under nitrogen. The reactions were checked by LIPLC the next morning, concentrated to dryness and diluted with 1 mL of DMSO. Pre-purification analysis in the LIPLC was done with water/acetonitrile/0.1% formic acid. Library purification was performed on the Waters purification/analytical LC/UV/ELSD system and parallel evaporations were carried out using a Genevac HT-24. Exemplary compounds 1-2, 5, 7, and 20 were obtained using methods described below, and shown in the general synthesis scheme above. The specific reaction sequence for each of the compounds 1-2, 5, 7, and 20 is shown preceding the characterization data for the compound immediately below. Additional characterization data for compounds 1- 103 is shown in Table 2 immediately following the Examples below.
With pyridine at 80℃; for 16h; Inert atmosphere; 3 GENERAL PROCEDURE FOR THE SYNTHESIS OF SULFONAMIDES. General procedure: In a 48 position Mettler Toledo XT reaction block containing 11 .5 x 110 mm test tubes equipped with a stir bar was added 0.1 mmol of 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline- 1 , 3-dione and the corresponding sulfonyl chloride (2.0 equiv, 0.2 mmol) for compounds 1-37 and 94-103, whereas 0.075 mmol of 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1 , 3-dione and the corresponding sulfonyl chloride (2.0 equiv, 0.15 mmol) for compounds 38-93 (see Table 2 immediately following the Examples below). Anhydrous pyridine (500 uL) was added and the reactions were heated in a reaction block to 80 °C and stirred overnight under nitrogen. The reactions were checked by LIPLC the next morning, concentrated to dryness and diluted with 1 mL of DMSO. Pre-purification analysis in the LIPLC was done with water/acetonitrile/0.1% formic acid. Library purification was performed on the Waters purification/analytical LC/UV/ELSD system and parallel evaporations were carried out using a Genevac HT-24. Exemplary compounds 1-2, 5, 7, and 20 were obtained using methods described below, and shown in the general synthesis scheme above. The specific reaction sequence for each of the compounds 1-2, 5, 7, and 20 is shown preceding the characterization data for the compound immediately below. Additional characterization data for compounds 1- 103 is shown in Table 2 immediately following the Examples below.

 

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