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Chemistry
Heterocyclic Building Blocks
Piperidines
dioxopiperidine
2-(2,6-Dioxopiperidin-3-yl)-4-iodoisoindoline-1,3-dione
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Piperidines
Indoles Indolines Ketones
dioxopiperidine
dione

[ CAS No. 959150-64-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
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Chemical Structure| 959150-64-2
Chemical Structure| 959150-64-2
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Quality Control of [ 959150-64-2 ]

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Product Details of [ 959150-64-2 ]

CAS No. :959150-64-2 MDL No. :MFCD31735040
Formula : C13H9IN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :VXDTWULFGNROJV-UHFFFAOYSA-N
M.W : 384.13 Pubchem ID :44435673
Synonyms :

Safety of [ 959150-64-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 959150-64-2 ]

* 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 [ 959150-64-2 ]

[ 959150-64-2 ] Synthesis Path-Downstream   1~79

  • 1
  • [ 959150-64-2 ]
  • [ 141-32-2 ]
  • C20H20N2O6 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5819 - 5824
  • 2
  • [ 959150-64-2 ]
  • [ 111-34-2 ]
  • C19H20N2O5 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5819 - 5824
  • 3
  • [ 88-12-0 ]
  • [ 959150-64-2 ]
  • C19H17N3O5 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5819 - 5824
  • 4
  • [ 959150-64-2 ]
  • [ 292638-85-8 ]
  • C17H14N2O6 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5819 - 5824
  • 5
  • [ 959150-64-2 ]
  • [ 930-68-7 ]
  • C19H16N2O5 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5819 - 5824
  • 6
  • [ 28418-88-4 ]
  • (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate [ No CAS ]
  • [ 959150-64-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5819 - 5824
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
[3]European Journal of Medicinal Chemistry,2021,vol. 217
  • 7
  • [ 959150-64-2 ]
  • [ 917-92-0 ]
  • [ 1216805-59-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 8
  • [ 959150-64-2 ]
  • [ 14918-21-9 ]
  • [ 1216805-65-0 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 9
  • [ 959150-64-2 ]
  • [ 71597-85-8 ]
  • [ 1216805-41-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 10
  • [ 959150-64-2 ]
  • [ 153624-46-5 ]
  • [ 1216805-45-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 11
  • [ 959150-64-2 ]
  • [ 107-19-7 ]
  • [ 1216805-67-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 12
  • [ 959150-64-2 ]
  • [ 536-74-3 ]
  • [ 1216805-61-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 13
  • [ 959150-64-2 ]
  • [ 115-19-5 ]
  • [ 1216805-62-7 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 14
  • [ 959150-64-2 ]
  • [ 153624-38-5 ]
  • [ 1216805-39-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 15
  • [ 959150-64-2 ]
  • [ 195062-57-8 ]
  • [ 1216805-37-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 16
  • [ 959150-64-2 ]
  • [ 149104-90-5 ]
  • [ 1216805-47-8 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 17
  • [ 959150-64-2 ]
  • [ 123088-59-5 ]
  • [ 1216805-44-5 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 18
  • [ 959150-64-2 ]
  • [ 98-80-6 ]
  • [ 1216805-36-5 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 650 - 662
  • 19
  • [ 959150-64-2 ]
  • 3-benzyl-9-methyl-2-((1-(pent-4-yn-1-yl)-1H-pyrazol-4-yl)ethynyl)-4H,6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,4]oxazepine [ No CAS ]
  • 4-(5-(4-((3-benzyl-9-methyl-4H,6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,4]oxazepin-2-yl)ethynyl)-1H-pyrazol-1-yl)pent-1-yn-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6685 - 6704
  • 20
  • [ 959150-64-2 ]
  • [ 87100-28-5 ]
  • 4-benzyl-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With [Pd2(dba)3]*CHCl3; triphenylphosphine; silver(l) oxide; In tetrahydrofuran; at 70.0℃;Inert atmosphere; Sealed tube; To a flame-dried reaction vial, 4-iodothalidomide (100 mg,0.26 mol), Pd2(dba)3CHCl3 (22 mg, 0.021 mmol), triphenylphosphine(68 mg, 0.26 mmol), Ag2O (121 mg, 0.52 mmol) were added.The vial was evacuated and backfilled with argon three times, thenfitted with a PTFE septum and THF (1.5 mL) was added, followed bybenzyl boronic acid pinacol ester (87 mL, 0.39 mmol). The reactionvial was sealed under argon and heated to reflux for 18 h withstirring. After cooling to room temperature solvent was removed invacuo and the residue was passed through a silica plug (20/50%ethyl acetate/hexanes), then purified by PTLC (50% ethyl acetate/hexanes) to afford the title compound as a white solid (61 mg, 67%).Rf 0.48 (50% ethyl acetate/hexanes); mp 195e197 C; 1H NMR(500 MHz, CDCl3) d 8.04 (s, 1H), 7.74 (d, J 7.3 Hz, 1H), 7.62 (t,J 7.6 Hz, 1H), 7.47 (d, J 7.8 Hz, 1H), 7.33e7.28 (m, 2H), 7.28e7.21(m, 4H), 4.99 (dd, J 12.4, 5.4 Hz, 1H), 4.49 (s, 2H), 2.94e2.70 (m,3H), 2.20e2.12 (m, 1H); 13C NMR (126 MHz, CDCl3) d 170.9, 168.1,168.0, 167.3, 147.4, 142.1, 136.4, 136.4, 134.4, 132.3, 129.2, 128.1,126.9, 122.0, 49.3, 36.3, 33.9, 31.5, 29.9, 25.0, 24.1, 22.8; IR (neat):3216 (N-H), 3084, 1770 (CO), 1700 (CO), 1601, 1388, 1322, 1256,1194, 1119, 737, 700 cm1; HRMS calculated for C20H17N2O4:349.1188, found: 349.1189 [MH].
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 21
  • [ 959150-64-2 ]
  • 2-(4-isopropylbenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(4-isopropylbenzyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With [Pd2(dba)3]*CHCl3; triphenylphosphine; silver(l) oxide; In tetrahydrofuran; at 70.0℃;Inert atmosphere; Sealed tube; General procedure: To a flame-dried reaction vial, 4-iodothalidomide (100 mg,0.26 mol), Pd2(dba)3CHCl3 (22 mg, 0.021 mmol), triphenylphosphine(68 mg, 0.26 mmol), Ag2O (121 mg, 0.52 mmol) were added.The vial was evacuated and backfilled with argon three times, thenfitted with a PTFE septum and THF (1.5 mL) was added, followed bybenzyl boronic acid pinacol ester (87 mL, 0.39 mmol). The reactionvial was sealed under argon and heated to reflux for 18 h withstirring. After cooling to room temperature solvent was removed invacuo and the residue was passed through a silica plug (20/50%ethyl acetate/hexanes), then purified by PTLC (50% ethyl acetate/hexanes) to afford the title compound as a white solid (61 mg, 67%).
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 22
  • [ 959150-64-2 ]
  • [ 4946-14-9 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-[(4-isopropylphenyl)sulfanyl]isoindole-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 23
  • [ 959150-64-2 ]
  • [ 62673-31-8 ]
  • 4-benzyl-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 24
  • [ 959150-64-2 ]
  • potassium benzyltrifluoroborate [ No CAS ]
  • 4-benzyl-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 25
  • [ 959150-64-2 ]
  • C10H13BF3(1-)*K(1+) [ No CAS ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(4-isopropylbenzyl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 26
  • [ 87-59-2 ]
  • [ 959150-64-2 ]
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 27
  • [ 31599-60-7 ]
  • [ 959150-64-2 ]
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 28
  • [ 959150-64-2 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-((4-isopropylphenyl)sulfonyl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 29
  • [ 959150-64-2 ]
  • 4-((4-(tert-butyl)phenyl)thio)-2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 30
  • [ 959150-64-2 ]
  • [ 62-53-3 ]
  • [ 927670-92-6 ]
YieldReaction ConditionsOperation in experiment
97% With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 31
  • [ 959150-64-2 ]
  • [ 99-88-7 ]
  • [ 927671-00-9 ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 32
  • [ 959150-64-2 ]
  • [ 108-98-5 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(phenylsulfanyl)isoindole-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.4.9.1. 2-(2,6-Dioxopiperidin-3-yl)-4-(phenylsulfanyl)isoindole-1,3-dione (5i)Following the above general procedure using thiophenol(32 mg, 0.29 mmol), the title compound was obtained after purificationvia flash column chromatography (40% ethyl acetate/hexanes)as a pale yellow solid (89 mg, 94%). mp 243e245 C; 1HNMR (400 MHz, DMSO-d6) d 11.16 (s, 1H), 7.94e7.27 (m, 7H), 6.94(dd, J 1 Hz, 1H), 5.17 (dd, J 12.8, 5.4 Hz, 1H), 2.91 (ddd, J 16.8,13.7 & 5.4 Hz, 1H), 2.69e2.53 (m, 2H), 2.16e2.03 (m, 1H); 13C NMR(126 MHz, DMSO-d6) d 172.8, 169.9, 166.7, 166.5, 139.0, 135.5, 135.2,132.4, 130.6, 130.5, 130.3, 128.1, 124.9, 119.8, 49.0, 31.0, 21.9; IR(neat) 3190, 1764 (CO), 1701 (CO), 1253, 1185, 743 cm1; HRMScalculated for C19H15N2O4S: 367.0753, found: 367.0762 [MH].
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 33
  • [ 959150-64-2 ]
  • [ 106-49-0 ]
  • C20H17N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 34
  • [ 959150-64-2 ]
  • [ 589-16-2 ]
  • C21H19N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 35
  • [ 959150-64-2 ]
  • [ 2696-84-6 ]
  • C22H21N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 36
  • [ 959150-64-2 ]
  • [ 769-92-6 ]
  • [ 927670-99-3 ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 37
  • [ 959150-64-2 ]
  • [ 104-13-2 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-[(4-butylphenyl)amino]isoindole-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.4.8.1. 2-(2,6-Dioxopiperidin-3-yl)-4-[(4-butylphenyl)amino]isoindole-1,3-dione (6g)Following the general procedure for Buchwald-Hartwig aminationreactions, using 4-butylaniline (123 mg, 0.79 mmol) the titlecompound was obtained after purification by flash column chromatography(30% / 50% ethyl acetate/hexanes) as a yellow solid(207 mg, 98%). Rf 0.33 (40% ethyl acetate/hexane);mp 205e207 C; 1H NMR (500 MHz, DMSO-d6) d 11.13 (s, 1H),8.33 (s, 1H), 7.58 (dd, J 8.6, 7.1 Hz, 1H), 7.34 (d, J 8.5 Hz, 1H), 7.21(dd, J 8.0, 5.3 Hz, 5H), 5.12 (dd, J 12.9 & 5.4 Hz, 1H), 2.90 (ddd,J 17.3, 14.0 & 5.4 Hz, 1H), 2.66e2.52 (m, 4H), 2.14e1.98 (m, 1H),1.56 (quint., J 7.4 Hz, 2H), 1.32 (sext., J 7.4 Hz, 2H), 0.90 (t,J 7.4 Hz, 3H); 13C NMR (126 MHz, DMSO) d 173.2, 170.5, 168.8,167.5, 143.8, 138.9, 137.3, 136.6, 132.9, 129.7, 122.9, 119.4,113.4, 111.8,49.1, 34.7, 33.6, 31.4, 22.6, 22.2, 14.2; IR (neat) 3324 (N-H) 3205 (NH),1757 (CO), 1689 (CO), 1619 (CO), 1401, 1320 cm1; HRMScalculated for C23H24N3O4: 406.1767, found: 406.1770 [MH].
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 38
  • [ 959150-64-2 ]
  • [ 123-30-8 ]
  • C19H15N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 39
  • [ 959150-64-2 ]
  • [ 104-94-9 ]
  • [ 927671-03-2 ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 40
  • [ 959150-64-2 ]
  • [ 7664-66-6 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-[(4-isopropoxyphenyl)amino]isoindole-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 41
  • [ 959150-64-2 ]
  • [ 99-98-9 ]
  • [ 927671-11-2 ]
YieldReaction ConditionsOperation in experiment
15% With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 42
  • [ 959150-64-2 ]
  • [ 455-14-1 ]
  • C20H14F3N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 43
  • [ 959150-64-2 ]
  • [ 99-92-3 ]
  • C21H17N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 44
  • [ 959150-64-2 ]
  • [ 94-09-7 ]
  • C22H19N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 45
  • [ 504-29-0 ]
  • [ 959150-64-2 ]
  • C18H14N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 46
  • [ 959150-64-2 ]
  • [ 95-53-4 ]
  • C20H17N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 47
  • [ 959150-64-2 ]
  • [ 2217-43-8 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(5,6,7,8-tetrahydronaphthalen-2-ylamino)isoindole-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With [Pd2(dba)3]*CHCl3; potassium carbonate; XPhos; In 1,4-dioxane; at 90.0℃; for 18.0h;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence, under an inert atmosphere of argon: 4-iodothalidomide(200 mg, 0.52 mmol), XPhos (40 mg, 0.083 mmol) Pd2(dba)3CHCl3(22 mg, 0.021 mmol) K2CO3 (144 mg, 1.04 mmol) 1,4-dioxane(2 mL) and The desired aniline (0.89 mmol). The reaction mixturewas stirred at 90 C for 18 h and the resulting mixture then cooledto room temperature, diluted with ethyl acetate (10 mL) andfiltered through a pad of Celite. The filter cake was washed withethyl acetate (ca. 40 mL) and the resulting filtrate adsorbed to silica.Purification by flash column chromatography (ethyl acetate/hexanes)gave the desired aminated thalidomide analogue.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 48
  • [ 959150-64-2 ]
  • [ 106-45-6 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(p-tolylthio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 49
  • [ 959150-64-2 ]
  • [ 2396-68-1 ]
  • 4-((4-(tert-butyl)phenyl)thio)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 50
  • [ 959150-64-2 ]
  • [ 825-83-2 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-((4-(trifluoromethyl)phenyl)thio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 51
  • [ 959150-64-2 ]
  • [ 696-63-9 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-((4-methoxyphenyl)thio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 52
  • [ 959150-64-2 ]
  • [ 1122-97-0 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-((4-(methylsulfanyl)phenyl)thio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 53
  • [ 959150-64-2 ]
  • [ 131242-36-9 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(pyrimidin-2-ylthio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
158 mg With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 54
  • [ 959150-64-2 ]
  • [ 2637-37-8 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(quinolin-2-ylthio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
188 mg With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 55
  • [ 959150-64-2 ]
  • [ 137-06-4 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(o-tolylthio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 56
  • [ 959150-64-2 ]
  • [ 108-40-7 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-(m-tolylthio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 57
  • [ 959150-64-2 ]
  • [ 76041-72-0 ]
  • 2-(2,6-dioxopiperidin-3-yl)-4-((5-(trifluoromethyl)pyridin-2-yl)thio)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
70 mg With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 58
  • [ 959150-64-2 ]
  • [ 100-53-8 ]
  • 4-(benzylthio)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 59
  • [ 959150-64-2 ]
  • [ 109-79-5 ]
  • 4-(butylthio)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 60
  • [ 959150-64-2 ]
  • [ 75-66-1 ]
  • 4-(tert-butylthio)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 61
  • [ 959150-64-2 ]
  • [ 1569-69-3 ]
  • 4-cyclohexylthio-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 62
  • [ 959150-64-2 ]
  • [ 34301-54-7 ]
  • 4-(adamantylthio)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With [Pd2(dba)3]*CHCl3; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90.0℃;Schlenk technique; Inert atmosphere; General procedure: To a flame-dried Schlenk flask was added the following insequence under an inert atmosphere of argon: 4-iodothalidomide4a (200 mg, 0.52 mmol), Pd2(dba)3CHCl3 (16 mg, 0.016 mmol)and XantPhos (16 mg, 0.032 mmol), 1,4-dioxane (2 mL), diisopropylethylamine(0.50 mL, 1.04 mmol) and the required thiol(0.57 mmol). The reaction mixturewas heated to 90 C with stirringfor 16 h, cooled to room temperature and diluted with ethyl acetate(10 mL). The mixture was filtered through a pad of Celite, washingwith ethyl acetate and DCM (ca. 20 mL each). The filtrate wasadsorbed to silica and purified via flash column chromatography onsilica to furnish the desired sulfide-functionalised thalidomidederivative.
Reference： [1]European Journal of Medicinal Chemistry,2021,vol. 217
  • 63
  • [ 959150-64-2 ]
  • N-(2-((2,6-dimethoxy-4-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)benzyl)amino)ethyl)pent-4-ynamide [ No CAS ]
  • N-(2-((2,6-dimethoxy-4-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)benzyl)amino)ethyl)-5-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)pent-4-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 12.0h;Inert atmosphere; Heating; To a solution of compound20(140 mg, 370 µmol) in DMF (2 mL) was added15a(180 mg, 370 µmol), Pd(PPh3)2Cl2(25.0 mg, 370 µmol), CuI (7.10 mg, 370 µmol) and DIPEA (1 mL). The flask was stirred under the argon at 50 C for 12 h. Then the mixture was diluted with EtOAc (15 mL) and washed with saturated NaCl solution (5 mL), dried over Na2SO4and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/ methanol 10:1) to afford compound21a(183 mg, 65%) as white solid. M.p. 142.1-143.5 C; IR (KBr): 2920, 2840, 1720, 1646, 1597, 1422, 1397, 1151, 1113, 740, 737 cm-1.1H NMR (400 MHz, CDCl3)δ7.89 (m, 1H), 7.75 (dd,J= 6.5, 1.9 Hz, 1H), 7.65 (m, 2H), 7.36 (m, 9H), 6.19 (s, 2H), 5.06 (s, 3H), 4.17 (m, 2H), 3.81 (s, 6H), 3.64 (m, 2H), 3.02 (t,J= 5.3 Hz, 2H), 2.79 (ddt,J= 18.1, 16.6, 6.3 Hz, 5H), 2.58 (t,J= 6.9 Hz, 2H), 2.25 (s, 3H), 2.16 (m, 1H).13C NMR (100 MHz, CDCl3)δ172.3, 171.4, 168.7, 166.7, 166.5, 159.9, 143.2, 138.4, 134.7, 134.1, 132.2, 130.6, 129.4, 128.5, 128.2, 127.0, 125.8, 122.9, 97.7, 91.2, 69.5, 56.6, 49.6, 40.2, 36.4, 35.2, 31.5, 22.8, 16.4, 16.4. HRMS (ESI) calculated for C43H42N4NaO8+[M+Na]+: 765.2895, found 762.2899.
65% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 12.0h;Inert atmosphere; Heating; Taking 21a as an example, to a solution of compound 20 (0.14g, 0.37mmol) in DMF (2mL) was added 15a (0.18g, 0.37mmol), Pd(PPh3)2Cl2(25mg, 0.037mmol), CuI (7.1 mg, 0.037 mmol)) and DIPEA (1 mL).The mixture was replaced with argon 3 times and stirred at 50C for 12 h.The mixture was then diluted with EtOAc (15 mL), and washed with saturated NaCl solution (5 mL), and subjected to Na2SO4 dry and concentrate under reduced pressure.The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 10:1 to 5:1) to obtain compound 21a (183 mg, 65%) as a white solid
Reference： [1]Bioorganic Chemistry,2021,vol. 111
[2]Patent: CN113105431,2021,A .Location in patent: Paragraph 0096-0098
  • 64
  • [ 959150-64-2 ]
  • N-(2-((2,6-dimethoxy-4-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)benzyl)amino)ethyl)hex-5-ynamide [ No CAS ]
  • N-(2-((2,6-dimethoxy-4-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)benzyl)amino)ethyl)-6-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)hex-5-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 12.0h;Inert atmosphere; Heating; General procedure: To a solution of compound20(140 mg, 370 µmol) in DMF (2 mL) was added15a(180 mg, 370 µmol), Pd(PPh3)2Cl2(25.0 mg, 370 µmol), CuI (7.10 mg, 370 µmol) and DIPEA (1 mL). The flask was stirred under the argon at 50 C for 12 h. Then the mixture was diluted with EtOAc (15 mL) and washed with saturated NaCl solution (5 mL), dried over Na2SO4and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/ methanol 10:1) to afford compound21a(183 mg, 65%) as white solid.
Reference： [1]Bioorganic Chemistry,2021,vol. 111
  • 65
  • [ 959150-64-2 ]
  • N-(2-((2,6-dimethoxy-4-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)benzyl)amino)ethyl)hept-6-ynamide [ No CAS ]
  • N-(2-((2,6-dimethoxy-4-((2-methyl-[1,1'-biphenyl]-3-yl)methoxy)benzyl)amino)ethyl)-7-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)hept-6-ynamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 12.0h;Inert atmosphere; Heating; General procedure: To a solution of compound20(140 mg, 370 µmol) in DMF (2 mL) was added15a(180 mg, 370 µmol), Pd(PPh3)2Cl2(25.0 mg, 370 µmol), CuI (7.10 mg, 370 µmol) and DIPEA (1 mL). The flask was stirred under the argon at 50 C for 12 h. Then the mixture was diluted with EtOAc (15 mL) and washed with saturated NaCl solution (5 mL), dried over Na2SO4and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/ methanol 10:1) to afford compound21a(183 mg, 65%) as white solid.
Reference： [1]Bioorganic Chemistry,2021,vol. 111
  • 66
  • [ 28418-88-4 ]
  • [ 2353-44-8 ]
  • [ 959150-64-2 ]
YieldReaction ConditionsOperation in experiment
80% With sodium acetate; acetic acid; at 120.0℃; for 6.0h; To a solution of 6-iodophthalic anhydride 19 (2.00 g, 7.30 mmol) in CH3COOH (100 mL) was added 3-aminopiperidine-2,6-dione 7 (935.2 mg, 7.30 mmol).The mixture was refluxed at 120C for 6 hours.The mixture was then diluted with EtOAc (200 mL) and washed with saturated HCl solution (1 N, 50 mL),dried over Na2SO4 and concentrated under reduced pressure.The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 50:1) to obtain compound 20 (2.24, 80%) as a white solid.
Reference： [1]Bioorganic Chemistry,2021,vol. 111
[2]Patent: CN113105431,2021,A .Location in patent: Paragraph 0093-0095
  • 67
  • [ 959150-64-2 ]
  • C44H46N10O5 [ No CAS ]
Reference： [1]Patent: CN113402520,2021,A
  • 68
  • [ 959150-64-2 ]
  • C44H44N10O6 [ No CAS ]
Reference： [1]Patent: CN113402520,2021,A
  • 69
  • [ 959150-64-2 ]
  • C44H48N10O6 [ No CAS ]
Reference： [1]Patent: CN113402520,2021,A
  • 70
  • [ 959150-64-2 ]
  • C18H15BrN2O4 [ No CAS ]
Reference： [1]Patent: CN113402520,2021,A
  • 71
  • [ 959150-64-2 ]
  • 2-(2,6-dioxo-3-piperidyl)-4-(5-hydroxypentyl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]Patent: CN113402520,2021,A
  • 72
  • [ 959150-64-2 ]
  • C18H19BrN2O4 [ No CAS ]
Reference： [1]Patent: CN113402520,2021,A
  • 73
  • [ 959150-64-2 ]
  • C18H18N2O6 [ No CAS ]
Reference： [1]Patent: CN113402520,2021,A
  • 74
  • [ 959150-64-2 ]
  • [ 5390-04-5 ]
  • 2-(2,6-dioxo-3-piperidyl)-4-(5-hydroxypent-1-ynyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In 1,2-dimethoxyethane; for 12.0h;Inert atmosphere; Reflux; Under the protection of nitrogen, compound S66 (166 mg, 0.45 mmol), compound S67 (38 mg, 0.45 mmol),PdCl2(PPh3)2 (16mg, 0.02mmol), cuprous iodide (4mg, 0.02mmol) were added to 10mL of DME in turn,After stirring to dissolve, triethylamine (182 mg, 1.8 mmol) was added, and the reaction was refluxed for 12 hours.After the reaction is complete, add 10 mL of water to the system, extract with ethyl acetate, and combine the organic phases.Wash with saturated brine, dry with anhydrous sodium sulfate, filter, collect the filtrate and concentrate to obtain a crude product.The crude product was separated and purified by silica gel column chromatography to obtain white solid compound S68 (60 mg, 41% yield).
Reference： [1]Patent: CN113402520,2021,A .Location in patent: Paragraph 0493-0496
  • 75
  • [ 959150-64-2 ]
  • [ 6089-09-4 ]
  • C18H14N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In 1,2-dimethoxyethane; for 12.0h;Inert atmosphere; Reflux; Under the protection of nitrogen, compound S66 (166 mg, 0.45 mmol), compound S72 (44 mg, 0.45 mmol),PdCl2(PPh3)2 (16mg, 0.02mmol), cuprous iodide (4mg, 0.02mmol) were added to 10mL of DME in turn,After stirring to dissolve, triethylamine (182 mg, 1.8 mmol) was added, and the reaction was refluxed for 12 hours. Reaction complete, Add 10 mL of water to the system, extract with ethyl acetate, combine the organic phases, and wash with saturated brine,Dry with anhydrous sodium sulfate, filter, collect the filtrate and concentrate to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain white solid compound S73 (68 mg, 45% yield).
Reference： [1]Patent: CN113402520,2021,A .Location in patent: Paragraph 0513-0516
  • 76
  • [ 959150-64-2 ]
  • 4-amino-5-fluoro-3-(5-(4-(pent-4-ynoyl)piperazin-1-yl)-1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one [ No CAS ]
  • 4-(5-(4-(2-(4-amino-5-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)-1H-benzo[d]imidazol-5-yl)piperazin-1-yl)-5-oxopent-1-yn-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80.0℃; for 12.0h; The specific preparation steps of compound 24a in the technical route are:Intermediate 23a (170mg, 0.37mmol) was dissolved in DMF (2mL), and then Intermediate 21 (142mg, 0.37mmol), Pd(PPh3)2Cl2 (18mg, 0.04mmol), CuI (7.1mg, 0.04mmol) were added in sequence ), DIPEA (1mL, 3.7mmol), the mixture was reacted at 80C for 12h.The raw materials were detected by TLC. After the raw materials disappeared, the reaction was stopped, cooled to room temperature, extracted with ethyl acetate (50 mL), washed with saturated brine (30 mL), the organic phase was collected, dried over Na2SO4, filtered, and concentrated to obtain a crude product.The crude product was purified by silica gel chromatography (CH2Cl2:CH3OH=30:1) to obtain compound 24a (172 mg, 65%) as a yellow solid.
Reference： [1]Patent: CN113527263,2021,A .Location in patent: Paragraph 0071-0074; 0079-0080
[2]Journal of Medicinal Chemistry,2021,vol. 64,p. 16497 - 16511
  • 77
  • [ 28418-88-4 ]
  • [ 24666-56-6 ]
  • [ 959150-64-2 ]
YieldReaction ConditionsOperation in experiment
79% With sodium acetate; acetic acid; for 12.0h;Reflux; General procedure: The specific preparation steps of intermediate 11 in the technical route are: adding 9-fluorophthalic anhydride 6 (3.30g, 20.0mmol) in CH3COOH (100mL) solution3-Aminopiperidine-2,6-dione 7 (3.30 g, 20.0 mmol).The mixture was refluxed for 12 hours.The mixture was then diluted with EtOAc (200 mL) and washed with saturated HCl solution (1N, 50 mL), dried over Na2SO4, and concentrated under reduced pressure.The residue was purified by column chromatography on silica gel (dichloromethane: methanol = 50:1) to obtain compound 8 (4.78 g, 80%) as a white solid.
Reference： [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 16497 - 16511
[2]Patent: CN113527263,2021,A .Location in patent: Paragraph 0025-0027; 0038-0039; 0071-0074
  • 78
  • [ 959150-64-2 ]
  • 4-amino-5-fluoro-3-(5-(4-(hex-5-ynoyl)piperazin-1-yl)-1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one [ No CAS ]
  • 4-(6-(4-(2-(4-amino-5-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)-1H-benzo[d]imidazol-5-yl)piperazin-1-yl)-6-oxohex-1-yn-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 16497 - 16511
  • 79
  • [ 959150-64-2 ]
  • 4-amino-5-fluoro-3-(5-(4-(hept-6-ynoyl)piperazin-1-yl)-1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one [ No CAS ]
  • 4-(7-(4-(2-(4-amino-5-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)-1H-benzo[d]imidazol-5-yl)piperazin-1-yl)-7-oxohept-1-yn-1-yl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2021,vol. 64,p. 16497 - 16511
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