[ CAS No. 2353-44-8 ] {[proInfo.proName]}

Name: 2353-44-8|3-Aminopiperidine-2,6-dione|98%
Brand: Ambeed
SKU: A178561
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Product Details of [ 2353-44-8 ]

CAS No. :	2353-44-8	MDL No. :	MFCD11506223
Formula :	C₅H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NPWMTBZSRRLQNJ-UHFFFAOYSA-N
M.W :	128.13	Pubchem ID :	134508
Synonyms :

Safety of [ 2353-44-8 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501	UN#:	3259
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2353-44-8 ]

* 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.

Upstream synthesis route of [ 2353-44-8 ]
Downstream synthetic route of [ 2353-44-8 ]

[ 2353-44-8 ] Synthesis Path-Upstream 1~4

1
[ 201230-82-2 ]
[ 2353-44-8 ]
[ 583-53-9 ]
[ 50-35-1 ]

Reference： [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5578 - 5581

2
[ 85-44-9 ]
[ 2353-44-8 ]
[ 50-35-1 ]

Reference： [1] European Journal of Pharmaceutical Sciences, 2016, vol. 83, p. 114 - 119

3
[ 641-70-3 ]
[ 2353-44-8 ]
[ 19171-18-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 3, p. 878 - 881

4
[ 340020-02-2 ]
[ 2353-44-8 ]
[ 19171-19-8 ]

Yield	Reaction Conditions	Operation in experiment
96.6%	With sodium acetate In acetonitrile for 4 h; Reflux	40.0 g (170.8 mmol) of ethyl 4-amino-1,3-dioxo-1,3-dihydro-2H-isomdole-2-carboxylate, 800 cm³ of acetonitrile, 28.4 g (342.0 mmol) of anhydrous sodium acetate, 28.1 g (170.7 mmol) of 3-aminopiperidine-2,6-dione are measured into a 1000 cm³ round-bottomed flask, then the suspension obtained in this way is heated to reflux temperature. The stirring is continued at unchanged temperature for 4 hours. The reaction mixture is concentrated to about 40 cm³ at 40 °C with the help of a vacuum. 800 cm³ of distilled water is added to the concentrated residue, which is then stirred at room temperature for 30 minutes. (The water may also be added at an earlier stage.) Following this the crystalline product is filtered, washed with 2x400 cm³ of distilled water, then dried at 50 °C in a vacuum until constant weight is achieved. In this way 45.10 g (96.6percent) of the product according to the title is obtained. Mp. : 314-315 °C (decomposes) IR (KBr): 3481 , 3378, 3248, 1752, 1703, 1635, 1362, 1197 cm ¹. 1H NMR (DMSO-d6, 400 MHz): δ = 11.10 (b, 1H), 7.47 (m, 1H), 7.02 (m, 1H), 7.00 (m, 1H), 5.06 (m, 1H), 2.89 (m, 1H), 2.58 (m, 1H), 2.56 (m, 1H), 2.03 (m, 1H) ppm. HPLC: Waters Acquity UPLC BEH C18; 2.1 x50 mm; 1.7 μm; 0.5 mL/min; 225 nm; 10/90 CH₃CN/0.1 percent HClO₄ (aq); 1.38 min (99.90percent).

Reference： [1] Patent: WO2017/134476, 2017, A1, . Location in patent: Page/Page column 16

[ 2353-44-8 ] Synthesis Path-Downstream 1~41

1
[ 31140-42-8 ]
[ 2353-44-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With water; sodium chloride; for 4h;Reflux;	To the reaction flask, 3 L of distilled water and 0.8 kg of sodium chloride were added to the solution, followed by stirring. Then, 140 g of 3-N-t-butoxycarbonylamino-2,6-dioxopiperidine (II) obtained by the method of Example 1 , And then heated under reflux to 4h. After cooling to room temperature overnight, 77 g of 3-amino-piperidine-2,6-dione (III) was filtered and the yield of the desired product (III) was 98%reaction
9.5 g	With hydrogenchloride; In tert-butyl methyl ether; water; at 0℃; for 0.333333h;	Dissolve the 3-aminopiperidine-2,6-dione prepared in step (4) in 200 mLMethyl tert-butyl ether,Cool and keep at 0 C, pass in hydrogen chloride gas, and react for 20min.Precipitation of a white solid,Filtration and drying gave 9.5 g of a white solid with a yield of 90%.

Reference： [1]Patent: CN105440012,2016,A .Location in patent: Paragraph 0023; 0026; 0027
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 421 - 425
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 878 - 881
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4075 - 4081
[5]Patent: CN110407807,2019,A .Location in patent: Paragraph 0032; 0041-0042

2
[ 4664-08-8 ]
[ 2353-44-8 ]
3-(5-aza-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2,6-dioxopiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With triethylamine In tetrahydrofuran for 36h; Heating / reflux;	4 1, 3-DIOXO-2- (2, 6-dioxopiperidin-3-yl) -5-azaisoindoline (11) was prepared specifically as follows. A mixture OF CBZ-AMINOGLUTARIMIDE (302 mg) and palladium hydroxide on carbon (20%) in 2-propanol (20 ml) was stirred under H2 for one day. The reaction mixture was filtered through celite and washed with 2- propanol and methanol. The combined filtrate was concentrated to afford crude 3- AMINO-1, 6-dioxopiperidine as syrup. To the flask containing 3-AMINO-1, 6- dioxopiperidine was added 3,4-pyridinedicarboxylic anhydride (205 mg), triethylamine (0.16 ml) and THF (10 ml). The mixture was refluxed for one and a half days. The solvent was removed under vacuum. The residue was purified by column chromatography using CH2CL2 : MeOH (10: 1) as eluent to afford azathalidomide (52 mg) in the yield of 17% from CBZ-AMINOGLUTARIMIDE as a pale purple solid: mp 233-235°C, LH NMR (DMSO) 8 11.18 (s, 1H), 9.21 (s, 1H), 9.17 (d, J = 4. 8 HZ, 1 H), 7.98 (d, J = 4. 8 HZ, 1 H), 5.23 (dd, J = 5. 4 HZ, J = 12. 8 HZ, 1 H), 2.96-2. 85 (m, 2 H), 2.60-2. 51 (m, 1 H), 2.12-2. 07 (m, 1 H); MS (CI/CH4) M/Z 259 [M] + ; Anal. Calcd for N204 : C, 55.60 ; H, 3.50 ; N, 16.21. Found: C, 55.36 ; H, 3.44 ; N, 15.94.

Reference： [1]Current Patent Assignee: P2D INC; GOVERNMENT OF THE UNITED STATES - WO2005/28436, 2005, A2 Location in patent: Page/Page column 34

3
[ 6007-85-8 ]
[ 2353-44-8 ]
5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5-(2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione (Method 2) [Show Image] 1.54 g thieno(3,4-c)furan-1,3-dione was dissolved in 20 mL of anhydrous THF, and 12.8 g of 3-aminopiperidine-2,6-dione was added. The reaction mixture was allowed to react at room temperature for 4h. Then, 2 g of CDI and a catalytic quantity of DMAP were added, and the reaction mixture was allowed to reflux for 6h untill a large amount of white solid precipitated. The solid was cooled and filtered to yield 2.1 g of the title product.

Reference： [1]Patent: EP1964842,2008,A1 .Location in patent: Page/Page column 29

4
[ 24666-55-5 ]
[ 2353-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In tetrahydrofuran; methanol at 20℃; for 2h;	8 7.86 g of benzyl 2,6-dioxopiperidin-3-yl carbamate were dissolved in 30 mL of THF and 30 mL of methanol. 0.786 g of 10% Pd/C catalyst was added to the above solution. The mixture was allowed to react under a flow of hydrogen at room temperature for 2h, filtered to remove the catalyst, and evaporated to remove the solvent. A light blue solid (3.818 g) was obtained.
	With hydrogen In tetrahydrofuran; methanol at 20℃; for 2h;	7 3-aminopiperidine-2,6-dione [Show Image] 7.86 g of benzyl 2,6-dioxopiperidin-3-yl carbamate were dissolved in 30 mL of THF and 30 mL of methanol. 0.786 g of 10% Pd/C were added to the above solution. The reaction mixture was allowed to react under a flow of hydrogen at room temperature for 2h, filtered to remove the catalyst, and evaporated to dryness to remove the solvent. A light blue solid (3.818 g) was obtained.

Reference： [1]Current Patent Assignee: HEMAY(HONG KONG) INVESTMENT LIMITED; TIANJIN HEMEY BIO TECH - EP2093228, 2009, A1 Location in patent: Page/Page column 13
[2]Current Patent Assignee: HEMAY(HONG KONG) INVESTMENT LIMITED - EP1964842, 2008, A1 Location in patent: Page/Page column 28

5
[ 5466-84-2 ]
[ 2353-44-8 ]
[ 55003-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	With glacial acetic acid Reflux; Molecular sieve;
	With anhydrous Sodium acetate; glacial acetic acid at 140℃; for 8h;	4.1.14. 2-(2,6-Dioxopiperidin-3-yl)-5-nitroisoindoline-1,3-dione (A21) A well stirred mixture of A20 (2.00 g, 10.36 mmol), 3-aminopiperidine-2,6-dione (1.46 g, 11.40 mmol) and sodium acetate (1.10 g, 13.47mmol) in acetic acid (20 mL) was heated to 140 C for 8 h. Cooling toroom temperature, the mixture was directly concentrated and purifiedby column chromatography to obtain intermediate A21.

Reference： [1]Location in patent: scheme or table Contino-Pépin, Christiane; Parat, Audrey; Périno, Sandrine; Lenoir, Christine; Vidal, Michel; Galons, Hervé; Karlik, Stephen; Pucci, Bernard [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 3, p. 878 - 881]
[2]Cheng, Maosheng; Qin, Qiaohua; Sun, Yin; Sun, Yixiang; Sun, Yu; Wang, Jingkai; Wang, Lin; Wang, Ruifeng; Wu, Tianxiao; Xue, Yanli; Yin, Wenbo; Zhao, Dongmei [European Journal of Medicinal Chemistry, 2022, vol. 237]

6
[ 641-70-3 ]
[ 2353-44-8 ]
[ 19171-18-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 878 - 881

7
[ 98475-07-1 ]
[ 2353-44-8 ]
[ 827026-45-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	In N,N-dimethyl-formamide; for 3h;Reflux;	2-Chloromethyl-3-nitrobenzoate (IV) 230g (1mol) and the compound (III) 173g (1.35mol) was dissolved in DMF2L.It was heated with stirring under reflux for 3h.Cooled to room temperature, poured slowly into ice-water and 50L, stirring was continued for 2h, filtered, washed with water and dried, to give the product compound (V) 277.6g, a yield of 96% (in terms of Compound IV).
79.5%		[00123] A nitrogen-purged 1600 L Hastelloy reaction vessel was charged with methyl-2- bromomethyl-3-nitrobenzoate (61 kg, 1.0 mole eq.), racemic a-aminoglutarimide (36.6 kg, 1.0 mole eq.), and acetonitrile (478 kg). The mixture was stirred at ambient temperature and then cooled to 5-8 C. Sodium bicarbonate (46.7 kg, 2.5 mole eq.) was charged to the reaction vessel and the mixture was heated to reflux. The reaction vessel contents were vigorously stirred at reflux until the remaining brominated nitrobenzoate level is <3.0 mol% as determined by 1H- NMR. The reaction mixture was then cooled to 58-62 C. [00124] A hydrochloric acid solution was prepared from concentrated hydrochloric acid (12.9 kg) and purified water (355 L) in a nitrogen-purged, stirred 1000 L Hastelloy vessel and heated to 58-62 C. A portion of this hydrochloric acid solution (329 L) was added to the reaction mixture in the 1600 L vessel over at least 10 minutes while maintaining the temperature at 58-62 C. The mixture was stirred for approximately 30 minutes, then pH of the reaction mixture was checked. If the pH was >6, 6.1 L aliquots of hydrochloric acid were added, while maintaining the temperature at approximately 58-62 C, until the pH of the reaction mixture was <6. The mixture was then cooled to ambient temperature over approximately 2.5 hours and stirred for an additional hour. [00125] The solid was collected by vacuum/pressure filtration on an Oyster filter. The collected solid was washed on the Oyster filter with a mixture of acetone (76 kg) and purified water (90 kg), and de-liquored using vacuum pressure. The collected solid was washed with 147 kg of acetone and de-liquored using vacuum pressure. The solid was dried under vacuum in a VPD at <45 C until loss on drying is <0.5% to provide 3-(4-nitro-l-oxoisoindolin-2- yl)piperidine-2,6-dione. The yield of a recent lot was 79.5%.
	With triethylamine; In N,N-dimethyl-formamide; at 25 - 100℃; for 7h;Inert atmosphere;	Preparation of 3-(4-nitro-l-oxo-l , 3 dihydro-isoindol-2-yl)-piperidine-2, 6-dione: Into a 2.0 L dried 4 necked round bottom flask equipped with a condenser, an addition funnel and nitrogen gas bubbler under stirring, charged 50.0 g of methyl 2- bromomethyl-3-nitro-benzoate, 29.2g of racemic 3-amino-piperidine-2,6-dione and 835.0 ml of DMF. Charged triethyl amine to the reaction mass at 25-35C in about 30-45 min. Raise the mass temperature to 95-100C. Maintained the reaction mass at 95-100C for 6-6 ½ hrs under nitrogen atmosphere. The progress of the reaction is monitored by TLC. Poured the reaction mass slowly into 2.6 L of DM water at 25-35C under stirring, in about 30-45 min. Maintained the reaction mass at 25-35C for 60-90 min under stirring. Filtered the material under vacuum, wash the wet cake with 215.0 ml of DM water, suck died the material. Dried the wet material in a oven at 60-65C for 4-5 hours. Weight of the dry material is- 30. Og.

With triethylamine; In N,N-dimethyl-formamide; at 75℃; for 20h;

To a solution of alpha-aminoglutarimide (1.0 equiv.) and methyl 2-(bromomethyl)-3- nitrobenzoate (1.3 equiv) in DMF is added triethylamine (3.0 equiv), and the mixture is heated to 75 C and stirred for 20 h. Then it is cooled to RT and poured into LiCl (5% in H2O). It is extracted with EtOAc, and the combined organic phases are washed with LiCl (5% in H2O) and saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated in vacuo. The crude is purified by column chromatography on silica gel to give 3-(7-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione. (Org. Lett., 2013, 15 (17), pp 4312-4315)

Reference： [1]Patent: CN105440012,2016,A .Location in patent: Paragraph 0023; 0031; 0032
[2]Patent: WO2013/126394,2013,A1 .Location in patent: Paragraph 00123-00125
[3]Patent: WO2011/111053,2011,A1 .Location in patent: Page/Page column 16
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4075 - 4081
[5]Patent: WO2017/197056,2017,A1 .Location in patent: Page/Page column 250

8
[ 201230-82-2 ]
[ 2353-44-8 ]
[ 583-53-9 ]
[ 50-35-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5578 - 5581

9
[ 85-44-9 ]
[ 2353-44-8 ]
[ 50-35-1 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;Microwave irradiation;	General procedure: A mixture of phthalic anhydride (2.5mmol, 0.37g), 2.5mmol of the corresponding amine and 0.1mL of DMF were subjected to microwave irradiation (Fig. 1). Reaction time and temperature varies for each derivative being synthesized. The reaction was monitored by TLC employing Cl2CH2: MeOH (8:2) as mobile phase. After complete conversion, the reaction mixture was triturated with ethanol and the solid product was recrystallized from a solvent mixture (EtOH: H2O, 2:1).

Reference： [1]European Journal of Pharmaceutical Sciences,2016,vol. 83,p. 114 - 119

10
[ 340020-02-2 ]
[ 2353-44-8 ]
[ 19171-19-8 ]

Yield	Reaction Conditions	Operation in experiment
96.6%	With sodium acetate; In acetonitrile; for 4h;Reflux;	40.0 g (170.8 mmol) of ethyl 4-amino-1,3-dioxo-1,3-dihydro-2H-isomdole-2-carboxylate, 800 cm3 of acetonitrile, 28.4 g (342.0 mmol) of anhydrous sodium acetate, 28.1 g (170.7 mmol) of 3-aminopiperidine-2,6-dione are measured into a 1000 cm3 round-bottomed flask, then the suspension obtained in this way is heated to reflux temperature. The stirring is continued at unchanged temperature for 4 hours. The reaction mixture is concentrated to about 40 cm3 at 40 C with the help of a vacuum. 800 cm3 of distilled water is added to the concentrated residue, which is then stirred at room temperature for 30 minutes. (The water may also be added at an earlier stage.) Following this the crystalline product is filtered, washed with 2x400 cm3 of distilled water, then dried at 50 C in a vacuum until constant weight is achieved. In this way 45.10 g (96.6%) of the product according to the title is obtained. Mp. : 314-315 C (decomposes) IR (KBr): 3481 , 3378, 3248, 1752, 1703, 1635, 1362, 1197 cm 1. 1H NMR (DMSO-d6, 400 MHz): delta = 11.10 (b, 1H), 7.47 (m, 1H), 7.02 (m, 1H), 7.00 (m, 1H), 5.06 (m, 1H), 2.89 (m, 1H), 2.58 (m, 1H), 2.56 (m, 1H), 2.03 (m, 1H) ppm. HPLC: Waters Acquity UPLC BEH C18; 2.1 x50 mm; 1.7 mum; 0.5 mL/min; 225 nm; 10/90 CH3CN/0.1 % HClO4 (aq); 1.38 min (99.90%).

Reference： [1]Patent: WO2017/134476,2017,A1 .Location in patent: Page/Page column 16

11
[ 41806-40-0 ]
[ 2353-44-8 ]
N-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-imidazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%		First 1-Methyl-1H-imidazole-5-carboxylic acid (128.1 mg, 1 mmol) in THF (1.0 mL) was treated with CO2Cl2 (86.86 muL, 1 mmol ) at C, 1 drop of DMF was added to the mixture and stirred for 2 h. The mixture was evaporated and the formation of acid chloride was confirmed by 1H NMR and the product was used in the next step. The 3-aminopiperidine-2,6-dione (128.1 mg, 1 mmol) in THF (1.0 mL) was added at 0 C to the acid chloride mixture. The reaction was stirred at r.t. for 2 h at r.t., diluted with EtOAc (5 mL), washed with brine. The aqueous layer was extracted with EtOAc (2 x 5 mL), and the combined organic layers was dried (Na2SO4), and concentrated. The crude product was purified using SiO2 chromatography with MeOH:DCM (gradient elution, product eluted with 10% MeOH) to obtain pure MA6-116 (25 mg, 11%). HPLC: 98.9% [tR = 6.02 min, gradient MeOH:water, 5-95% with 0.1% TFA, 20 min]. ].1H NMR (400 MHz, DMSO-d6): delta 10.86 (s, 1H), 8.54 (d, J = 8.4 Hz, 1H), 7.77 (s, 1H), 7.61 (s, 1H), 4.73-4.66 (m, 1H), 3.81 (s, 3H), 2.81-2.73 (m, 1H), 2.55 (m, 1H), 2.10-2.04 (m, 1H), 1.95 (m, 1H); HPLC-MS (ESI): m/z 237 (M+H)+.

Reference： [1]Patent: WO2017/161119,2017,A1 .Location in patent: Page/Page column 128

12
[ 2353-44-8 ]
[ 337536-14-8 ]
3-(4-bromo-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine; In acetonitrile; at 80℃; for 12h;	The P4 (2.68g, 8.7mmol) and 3-amino-piperidine-2,6-dione (2.57g, 11.3mmol) was dissolved in CH3CN (30mL), TEA (2.8mL, 7.57mmol), refluxed for 12h 80 . TLC detected the end of the reaction. The reaction solution was extracted with ethyl acetate and water, the organic layer was rotary evaporation to give a white solid P5, 73% yield.
30 mg	With triethylamine; In acetonitrile; at 60℃; for 10h;	EXAMPLE 6 Synthesis of 3-(4-(5-aminopentyl)- l-oxoisoindolin-2-yl)piperidine-2,6-dione Step 1: Synthesis of S23 To a round -bottom flask, <strong>[337536-14-8]methyl 3-bromo-2-(bromomethyl)benzoate</strong> (50 mg) and Et3N (60 mg) were added to a solution of 3-aminopiperidine-2,6-dione (30 mg) in CH3CN (5 mL). The mixture was stirred for 10 hours at 60 C and purified by flash column chromatography to yield S23 in 30 mg. ESI-MS calculated for Ci3Hi2BrN203 [M+H]+ = 323.0; Observed: 323.2.
2.8 g	With potassium carbonate; In N,N-dimethyl-formamide; at 45℃;	Example 5: Illustrative Preparation of Lenolidomide analogs (1902) Scheme 8: Preparation of 3-(4-Bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione (Compound (1903) To a mixture of <strong>[337536-14-8]methyl 3-bromo-2-(bromomethyl)benzoate</strong> 8-1 (500 mg, 1.62 mmol) 3- aminopiperidine-2,6-dione (248 mg, 1.94 mmol) and potassium carbonate (279 mg, 2.02 mmol) in DMF (2.5mL ) being heated to 45 .The mixture was left standing overnight. LCMS showed the reaction. The reaction mixture was stirred for 2 hours at 45C and cooled to 20C to 25C. De- ionized water (2.5ml) was added to the reaction mixture at 20C to 25C and stirred for 15 minutes to 20 minutes. The solid obtained was filtered, washed with de-ionized water (2 x 5 ml) and dried under vacuum at 40C to 45C for 20 hours to obtain Compound 296 3-(4-bromo-1- oxoisoindolin-2-yl)piperidine-2,6-dione (2.80 g, 8.66 mmol) as white soild. 1H NMR (500 MHz, DMSO-d6): delta 11.02 (s, 1H), 7.88 (d, J=8 Hz ,1H), 7.78 (d, J=7.5Hz, 1H), 7.53(t, J=7.5Hz, 1H), 5.17-5.13 (m, 1H), 4.44 (d, J=18Hz, 1H), 4.28 (d, J=18, 1H), 2.95-2.88 (m, 1H), 2.62 (d, J=1.5, 1H), 2.51-2.46 (m, 1H), 2.04-2.01 (m, 1H). ES-MS (m/z): 322.91 (M + H+)

Reference： [1]Patent: CN110078725,2019,A .Location in patent: Paragraph 0048-0079; 0087-0089
[2]Patent: WO2017/176958,2017,A1 .Location in patent: Paragraph 0867-0868
[3]Patent: WO2017/197051,2017,A1 .Location in patent: Page/Page column 485-486

13
[ 2597-56-0 ]
[ 2353-44-8 ]
N-(2,6-dioxo-3-piperidyl)-2-methoxy-4-nitrobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.35%	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	1 Step 1: Preparation of Compound 106 2-Methoxy-4-nitro-benzoic acid (474.33 mg, 2.41 mmol) and 3-aminopiperidine-2,6- dione (330 mg, 2.00 mmol, HCl) mixed in DMF (5 mL) at 0oC, followed by HATU (991.06 mg, 2.61 mmol) and diisopropylethylamine (777.37 mg, 6.01 mmol, 1.05 mL) . The reaction mixture was stirred at room temp for 2 hrs, from [15:34]. HPLC and MS indicate all starting materials were consumed and product present as the main peak. Dilute with 15 mL EtOAc, isolate via filtration. cake was washed by water 3 times (10 mL each). Obtain compound 106 as white solid N-(2,6- dioxo-3-piperidyl)-2-methoxy-4-nitro-benzamide (495 mg, 1.61 mmol, 80.35% yield) 1H NMR (400 MHz, DMSO-d6) δ 10.88 (s, 1H), 8.73 (d, J = 7.8 Hz, 1H), 8.02- 7.80 (m, 2H), 4.76 (dt, J = 11.5, 6.9 Hz, 1H), 4.00 (s, 3H), 2.77 (ddd, J = 24.3, 12.4, 6.5 Hz, 1H), 2.54 (d, J = 3.8 Hz, 1H), 2.23- 2.00 (m, 2H). LC MS: ES+ 308.2

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC - WO2017/197051, 2017, A1 Location in patent: Page/Page column 282-283

14
[ 6018-41-3 ]
[ 2353-44-8 ]
methyl 1-(2,6-dioxopiperidin-3-yl)-6-oxo-1,6-dihydropyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.1%	With triethylamine; In methanol; at 23℃; for 16h;Inert atmosphere;	Scheme 27: Synthesis of Compound 206 (1329) A solution of <strong>[6018-41-3]methyl coumalate</strong> 27-1 (200 mg, 1 equiv.) in MeOH (12 ml) was treated with 3-aminopiperidine-2,6-dione 27-2 (216 mg, 1.2 equiv.) and TEA (196 uL, 1.5 equiv.). The reaction was stirred at 23 C under nitrogen. After 16 h, the reaction was concentrated and triturated with MTBE:Ethylacetate mixture, The solid was suspended in acetonitrile:water, frozen and lyophilized, affording methyl 1-(2,6-dioxopiperidin-3-yl)-6-oxo-1,6-dihydropyridine-3- carboxylate (Compound 206) (86 mg, 23.1 %). (M+H).1H NMR (400 MHz, DMSO-d6) delta 11.04 (s, 1H), 8.46 (d, J = 2.5 Hz, 1H), 7.79 (dd, J = 9.6, 2.5 Hz, 1H), 6.44 (d, J = 9.6 Hz, 1H), 5.45 (s, 1H), 3.75 (s, 3H), 2.73 (s, 1H), 2.66- 2.45 (m, 2H), 2.11- 1.87 (m, 1H). LCMS: MS (ESI+): 265.2

Reference： [1]Patent: WO2017/197051,2017,A1 .Location in patent: Page/Page column 336

15
[ 586330-18-9 ]
[ 2353-44-8 ]
tert-butyl 3-((2,6-dioxopiperidin-3-yl)amino)-6-nitro-1H-indazole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 18h; Inert atmosphere;	3.1 Step 1: (1492) Following a general procedure from patent application WO2010007944: 3- aminopiperidine-2,6-dione (1 equiv.), tert-butyl 3-iodo-6-nitro-1H-indazole-1-carboxylate (1 equiv.) and cesium carbonate (2 equiv.) are mixed with dioxane (0.2M). The mixture is purged with N2 for 10 min. Palladium acetate (0.1 equiv.) and XANTPHOS (0.1 equiv.) are added to the mixture and the mixture is heated at 90 °C for 18 hours. The reaction mixture is cooled to ambient temperature and concentrated under vacuum. The residue is diluted with water and extracted with ethyl acetate (thrice). The organic layers are combined, dried over sodium sulfate and concentrated under vacuum. The residue is purified by flash chromatography on a silica gel column to provide tert-butyl 3-((2,6-dioxopiperidin-3-yl)amino)-6-nitro-1H-indazole-1-carboxylate.

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC - WO2017/197051, 2017, A1 Location in patent: Page/Page column 377-378

16
[ 782501-25-1 ]
[ 2353-44-8 ]
tert-butyl 4-(N-(2,6-dioxopiperidin-3-yl)sulfamoyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 4h;	To a stirred solution of 3-aminopiperidine-2,6-dione (1 equiv.) in DCM (0.2 M) are added triethylamine (3 equiv.) and <strong>[782501-25-1]tert-butyl 4-(chlorosulfonyl)piperidine-1-carboxylate</strong> (1.1 equiv.) sequentially at 0 C. The resulting mixture is stirred at the same temperature for 4 hours. The reaction mixture is then quenched with ice-water and extracted with EtOAc. The combined organics is washed with aqueous saturated NaHCO3 solution, water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue is purified by column chromatography to afford tert-butyl 4-(N-(2,6-dioxopiperidin-3-yl)sulfamoyl)piperidine-1- carboxylate.

Reference： [1]Patent: WO2017/197051,2017,A1 .Location in patent: Page/Page column 391-392

17
[ 782501-25-1 ]
[ 2353-44-8 ]
N-(2,6-dioxopiperidin-3-yl)piperidine-4-sulfonamide [ No CAS ]

Reference： [1]Patent: WO2017/197051,2017,A1

18
[ 59382-59-1 ]
[ 2353-44-8 ]
[ 827026-45-9 ]

Yield	Reaction Conditions	Operation in experiment
90.7%	With N,N,N,N,-tetramethylethylenediamine; zinc dibromide; In 1,4-dioxane; at 95℃;	1) 19.5 g (100 mmol) of <strong>[59382-59-1]methyl 2-methyl-3-nitrobenzoate</strong>,3-Amino-2,6-piperidinedione 15.4 g(120 mmol), 58.1 g (500 mmol) of tetramethylethylenediamine,45.8 g (150 mmol) of zinc bromide was added to the reaction vessel,250 ml of 1,4-dioxane was added and the mixture was heated to 95 C for 10 to 16 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure.Water washing and recrystallization (petroleum ether: dichloromethane = 10: 1) afforded 3-(4-nitro-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione 26.2 g,The yield was 90.7%, HPLC purity 99.51%;

Reference： [1]Patent: CN107337666,2017,A .Location in patent: Paragraph 0025; 0030-0032; 0034-0036; 0038-0040; 0042-0044

19
[ 37418-88-5 ]
[ 2353-44-8 ]
[ 5054-59-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 70℃; for 96h;	P6 (6.5 g, 40 mmol) was dissolved in dry DCM (50 mL), and 3-aminopiperidine-2,6-dione (5.12 g, 40 mmol)TEA (3 mL) and catalytic amount of DMAP were added and reacted at 70 C for 24 hours. Further, DCC (8.24 g, 40 mmol) and a catalytic amount of DMAP were added to the reaction mixture, and the mixture was reacted at 70 C for 72 hours. The reaction was completed by TLC, and a large amount of white solid was precipitated by adding water to the reaction mixture, filtered, and the filter cake was reconstituted with water, filtered, and then lyophilized. The product P7 was a pale yellow powder in a yield of 73%.
67%	With potassium acetate; acetic acid; at 120℃; for 1h;	4-Hydroxyisobenzofuran-l,3-dione (3.6 g, 22mmol), 3-aminopiperidine-2,6-dione (3.6 g, 22mmol) and KOAc (8.6 g, 88 mmol) were dissolved in acetic acid (70 mL). The reaction mixture was stirred at 120 C for 1 hour then cooled and diluted with water (100 mL). The resulting mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with NaHC03 and brine, dried (Na2S04) and filtered. The solvents were removed and the solid dried under vacuum to give the title compound (4.0 g, 67% yield) as a blue solid. 1H NMR (400 MHz, DMSO): delta 11.30 (br s, 1H), 11.10 (s, 1H), 7.65 (dd, 1H), 7.30 (d, 1H), 7.24 (d, 1H), 5.07 (m, 1H), 2.87 (m, 1H), 2.53 (m, 2H), 2.02 (m, 1H).
67%	With potassium acetate; acetic acid; at 120℃; for 1h;	4-Hydroxyisobenzofuran-l,3-dione (3.6 g, 22 mmol), 3-aminopiperidine-2,6-dione (3.6 g, 22 mmol) and KOAc (8.6 g, 88 mmol) were dissolved in acetic acid (70 mL). The reaction mixture was stirred at 120 C for 1 hour then cooled and diluted with water (100 mL). The resulting mixture was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with NaHCCb and brine, dried over Na2S04 and filtered. The solvents were removed under reduced pressure to give the title compound (4.0 g, 67% yield) as a blue solid. (0361) [0120] NMR (400 MHz, DMSO): d 11.30 (br s, 1H), 11.10 (s, 1H), 7.65 (dd, 1H), 7.30 (d, 1H), 7.24 (d, 1H), 5.07 (m, 1H), 2.87 (m, 1H), 2.53 (m, 2H), 2.02 (m, 1H).

Reference： [1]Patent: CN110078725,2019,A .Location in patent: Paragraph 0048; 0079; 0090-0092
[2]Patent: WO2018/85247,2018,A1 .Location in patent: Paragraph 00336
[3]Patent: WO2020/69105,2020,A1 .Location in patent: Paragraph 0119-0120
[4]Patent: WO2020/81446,2020,A1 .Location in patent: Paragraph 0167

20
[ 6007-85-8 ]
[ 2353-44-8 ]
5-(1-methyl-2,6-dioxopiperidin-3-yl)-5H-thieno(3,4-c)pyrrole-4,6-dione [ No CAS ]

Reference： [1]Patent: EP1964842,2008,A1

21
[ 14381-42-1 ]
[ 2353-44-8 ]
N-(2,6-dioxo-3-piperidyl)indane-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h;	2 Example 2 V-(2,6-Dioxopiperidin-3-yl)-2,3-dihydro-lH-indene-l-carboxamide (RACEMIC MIXTURE OF ALL DIASTEREOMERS) To a stirred suspension of 2,3-dihydro-lH-indene-l-carboxylic acid (100 mg), N,N- diisopropylethylamine (323 μ) and 3-aminopiperidine-2,6-dione60 (86.9 mg) in DMF (1.5 ml) was added HATU (352 mg). The reaction mixture was stirred at room temperature for 18 hours. The resulting yellow solution was directly purified by reversed phase HPLC to afford after lyophilisation N-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-lH-indene-l-carboxamide (RACEMIC MIXTURE OF ALL DIASTEREOMERS) as a white solid (168 mg, 66%). MS (ISP): 273.5 ([M+H]+).

Reference： [1]Current Patent Assignee: C4 THERAPEUTICS INC - WO2019/43214, 2019, A1 Location in patent: Page/Page column 44

22
[ 2353-44-8 ]
[ 827026-45-9 ]

Reference： [1]Patent: CN109400579,2019,A
[2]Patent: CN109400579,2019,A
[3]Patent: CN109400579,2019,A
[4]Patent: CN109400579,2019,A
[5]Patent: CN109400579,2019,A
[6]Patent: CN109400579,2019,A
[7]Patent: CN109400579,2019,A
[8]Patent: CN109400579,2019,A
[9]Patent: CN109400579,2019,A
[10]Patent: CN109400579,2019,A
[11]Patent: CN109400579,2019,A

23
[ 74530-56-6 ]
[ 2353-44-8 ]
3-(2,4-dioxopyrrolidin-1-yl)piperidine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 35 - 125℃; for 7.0h;Inert atmosphere; Reflux;	Under a nitrogen atmosphere, 140 g of N,N-dimethylformamide and 12.8 g (0.1 mol) were placed in a 500 ml four-necked flask equipped with a stirring, thermometer and air condenser.3-aminopiperidine-2,6-dione,21.5 g (0.11 mol) of 1-chloroacetoacetic acid tert-butyl ester,40 g of potassium carbonate, stirred at 35 to 40 C for 4 hours,The reaction was stirred at 120 to 125 C for 3 hours.Distilling off the tert-butanol formed by the amidation reaction; cooling to 40 C,21.5 (0.11 mol) of 2-bromo-4-nitro-n-butyraldehyde was added, and the reaction was stirred at 40 to 45 C for 5 hours.Filtered, the filter cake was washed with 40 g of N,N-dimethylformamide.Combine the filtrate,Distillation of N,N-dimethylformamide, addition of 90 g of isopropanol, recrystallization,26.9 g of 3-(7-nitro-3-oxo-1H-isoindol-2-yl)piperidine were obtained -2,6-dione, yield 93.0%, liquid phase purity 99.2%.

Reference： [1]Patent: CN109400579,2019,A .Location in patent: Paragraph 0061; 0062

24
[ 82-73-5 ]
[ 2353-44-8 ]
4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium acetate; acetic acid at 140℃; for 12h;	45 Preparation of 4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (SIAIS 172136): According to Scheme 14, the substrate 4-bromoisobenzofuran-1,3-dione (500 mg, 2.20 mmol),3-Aminopiperidine-2,6-dione (400 mg, 2.42 mmol) was added to a 100 mL egg-shaped bottle together with anhydrous sodium acetate (220 mg, 2.64 mmol).Glacial acetic acid (10 mL) was then added.The reaction was then slowly warmed to 140 ° C and stirred for 12 h.After the reaction was completed, the reaction solution was cooled to room temperature, and a large amount of white solid precipitated;After suction filtration, the filter cake, water (10 mL) and methanol (2 mL) were added together in an egg-shaped bottle.Stir well for 0.5 h, then suction filtration, and the filter cake was washed with water.Dried under reduced pressure to give compound (SIAIS172136), the product as a white solid, 700mg, 94% yield.
94%	With sodium acetate; acetic acid at 140℃; for 12h;	48 Based on Scheme 17, Preparation of 4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (SIAIS172136) Based on Scheme 17, Preparation of 4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (SIAIS172136) In a 100 mL of round-bottom flask, to a stirred solution of 4-bromoisobenzofuran-1,3-dione (500 mg, 2.20 mmol) and 3-aminopiperidine-2,6-dione (400 mg, 2.42 mmol) in acetic acid (10 mL) was added anhydrous sodium acetate (220 mg, 2.64 mmol). After addition, the mixture was stirred for 12 h at 140° C. The mixture was cooled to room temperature, filtered, and the obtained solid was mixed with water (10 mL) and methanol (2 mL), and stirred for another 30 min, then filtered, washed with water, dried under reduced pressure to afford desired product (SIAIS172136) as a white solid (700 mg, 94% yield). 1H NMR (500 MHz, DMSO) δ 11.14 (s, 1H), 8.14 (d, J=1.4 Hz, 1H), 8.09 (dd, J=7.9, 1.7 Hz, 1H), 7.86 (d, J=7.9 Hz, 1H), 5.16 (dd, J=12.9, 5.4 Hz, 1H), 2.93-2.85 (m, 1H), 2.65-2.50 (m, 2H), 2.08-2.04 (m, 1H). HRMS (ESI) m/z: calcd C13H10BrN2O4+ [M+H]+, 336.9818; found, 336.9810.
94%	With sodium acetate; acetic acid at 140℃; for 12h;	4.1.27. 4-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione(S18) 4-bromoisobenzo -furan-1, 3-dione S17 (500 mg, 2.20 mmol), 3-aminoperidol 2, 6-dione (400 mg, 2.42 mmol) and anhydrous sodiumacetate (220 mg, 2.64 mmol) were added to a 100 ml egg-likebottle, followed by glacial acetic acid (10 ml). The reaction solutionwas then slowly raised to 140 C and stirred for 12 h. After thereaction was finished, the reaction liquid was reduced to roomtemperature and a large amount of white solid was precipitated.After filtrated the solvent, the solidwaswashed with the mixture ofwater (10 mL) and methanol (2 mL) fully stirred for 0.5 h. thenfiltration, the filter cake was washed with water to afford dryingcompound S18, white solid, 700 mg, (yield 94%). 1H NMR (500 MHz,DMSO-d6) d 11.14 (s, 1H), 8.14 (d, J 1.4 Hz, 1H), 8.09 (dd, J 7.9,1.7 Hz, 1H), 7.86 (d, J 7.9 Hz, 1H), 5.16 (dd, J 12.9, 5.4 Hz, 1H),2.93e2.85 (m, 1H), 2.65e2.50 (m, 2H), 2.08e2.04 (m, 1H). HRMS(ESI) m/z: calcd C13H10BrN2O4 [MH], 336.9818; found, 336.9810.

Reference： [1]Current Patent Assignee: SHANGHAITECH UNIVERSITY - CN109912655, 2019, A Location in patent: Paragraph 0470-0472
[2]Current Patent Assignee: SHANGHAITECH UNIVERSITY - US2020/407342, 2020, A1 Location in patent: Paragraph 0228-0228
[3]Liu, Haixia; Ding, Xinyu; Liu, Linyi; Mi, Qianglong; Zhao, Quanju; Shao, YuBao; Ren, Chaowei; Chen, Jinju; Kong, Ying; Qiu, Xing; Elvassore, Nicola; Yang, Xiaobao; Yin, Qianqian; Jiang, Biao [European Journal of Medicinal Chemistry, 2021, vol. 223]

25
[ 86-90-8 ]
[ 2353-44-8 ]
[ 26166-92-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium acetate; acetic acid; at 120℃; for 5h;	[0176] A solution of 5-bromoisobenzofuran-l,3-dione (2.0 g, 8.8 mmol), 3- aminopiperidine-2,6-dione (1.4 g, 8.8 mmol) and AcONa (1.4 g, 17.6 mmol) in AcOH (25 mL) was heated at l20C for 5 h. The mixture was concentrated, and the residue was washed with water followed by MeOH and DCM to give 5-bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-l,3- dione (2.7 g, 90% yield) as a solid. MS (ESI) m/z 359.0 [M+Na]+.
81%	With triethylamine; In acetonitrile; at 80℃; for 12h;	5-Bromo-benzofuran-1,3-dione (P1) (2.93 g, 8.7 mmol) and 3-aminopiperidine-2,6-dione (2.57 g, 11.3 mmol) were dissolved in CH3CN (30 mL) ), TEA (2.8 mL, 7.57 mmol), refluxed at 80 C for 12 h. TLC detected the end of the reaction. The reaction solution was extracted with ethyl acetate and water, the organic layer was rotary evaporation to give a white solid P2, 81% yield.

Reference： [1]Patent: WO2019/241274,2019,A1 .Location in patent: Paragraph 0176
[2]Patent: CN110078725,2019,A .Location in patent: Paragraph 0048; 0079; 0081-0083

26
methyl 2-chloromethyl-3-nitrobenzoate [ No CAS ]
[ 2353-44-8 ]
[ 827026-45-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With ammonium hydroxide; In N,N-dimethyl-formamide; for 2h;Reflux;	0.1 mol of methyl 2-chloromethyl-3-nitrobenzoate prepared in step (1) and 16.5 gThe 3-aminopiperidine-2,6-dione prepared in step (5) is dissolved in 200 mL of DMF,Add 5 mL of concentrated ammonia water and heat to reflux for 2 h. Cool to room temperature, introduce into ice water,A pale yellow solid precipitated, filtered, washed twice with distilled water, and dried.21.7 g of reaction product was obtained in a yield of 75%.

Reference： [1]Patent: CN110407807,2019,A .Location in patent: Paragraph 0032; 0043-0044

27
[ 56-85-9 ]
[ 2353-44-8 ]

Reference： [1]Patent: CN110407807,2019,A

28
[ 77112-53-9 ]
[ 2353-44-8 ]
N-(2,6-dioxopiperidin-3-yl)imidazo[1,2-a]pyrazine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With 1-methyl-1H-imidazole; 2-chloro-1-methyl-pyridinium iodide; In N,N-dimethyl-formamide; at 80℃; for 0.25h;Inert atmosphere; Microwave irradiation; Sealed tube; Green chemistry;	General procedure: Imidazo[1,2-a]pyrazine-2-carboxylic acid (5) (1.0 equiv.) Mukaiyama?s reagent and 2-chloro-1-methylpyridinium iodide (1.2 equiv.) were suspended in DMF (5.0 mL) under nitrogen atmosphere. Into the reaction mixture, aliphatic/aromatic amines (6a-l) (1.0 equiv.) and 1-methylimidazole (2.0 equiv.) were added. A homogeneous solution was formed after a gentle stirring. The reaction mixture was sealed in a microwave glass reactor and then irradiated by microwave oven at a constant temperature of 80 C with continuous stirring (1 min ramp, 15 min reaction time). After the reaction was completed, the solvent was removed through a rotary evaporator and the resulting residue was extracted by a biphasic system of 45 mL diethyl ether and 45 mL water. After the layer separation, the ether layer was dried by anhydrous sodium sulphate, followed by an evaporation of ether to get compounds 7a-l (Scheme-I).

Reference： [1]Asian Journal of Chemistry,2020,vol. 32,p. 84 - 90

29
[ 37795-77-0 ]
[ 2353-44-8 ]
2-amino-N-(2,6-dioxopiperidin-3-yl)-5-methoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap;	[12-2] Synthesis of 2-amino-N-(2,6-dioxopiperidin-3-yl)-5-methoxybenzamide (Compound <12-3>) To <strong>[37795-77-0]6-methoxy-2H-benzo[d][1,3]oxazine-2,4(1H)-dione</strong> (0.2 g, 1.04 mmol) dissolved in DMF (2 ml), 3-aminopiperidine-2,6-dione (0.2 g, 1.56 mmol) and DMAP (0.013 g, 0.104 mmol) were added, and the mixture was heated at 60 C. overnight. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried on Na2SO4. The crude compound was obtained as a blue solid (0.2 g) and this was used in the next step without further purification.

Reference： [1]Patent: US2020/62730,2020,A1

30
[ 20829-96-3 ]
[ 2353-44-8 ]
[ 1015474-85-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap;	[3-2] Synthesis of 2-amino-6-chloro-N-(2,6-dioxopiperidin-3-yl)benzamide (Compound <3-3>) To the solution of <strong>[20829-96-3]5-chloro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione</strong> (200 mg, 1.01 mmol) dissolved in DMF (4 ml), 3-aminopiperidine-2,6-dione (194 mg, 1.5 mmol) and DMAP (12 mg, 0.10 mmol) were added, and the temperature was elevated from 60 C. overnight. The reaction mixture was extracted with ethyl acetate and the organic layer was dried on Na2SO4. The crude compound was obtained as a blue solid (75 mg), and this was used in the next step without further purification. MS found (M+H)+ (m/z), 282.09; calcd for C12H9ClN4O3 m/z, 282.10.

Reference： [1]Patent: US2020/62730,2020,A1 .Location in patent: Paragraph 0125; 0131-0133

31
[ 20877-81-0 ]
[ 2353-44-8 ]
[ 1015474-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In N,N-dimethyl-formamide at 60℃;	5.2 Step 2: Preparation of 2-amino-N-(2,6-dioxopiperidin-3-yl)-6-methylbenzamide 3-Aminopiperidine-2,6 in 5-methyl-2H-bento [d] [1,3] oxazin-2,4 [1h] -dione (178mg, 1.01mmol) solution dissolved in DMF (4mL) -Dion (194 mg, 1.5 mmol) and DMAP (12 mg, 0.104 mmol) were added, and the mixture was warmed at 60 ° C overnight. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried over Na2SO4. The crude compound was obtained as a blue solid (50 mg), which was used in the next step without further purification.
	With dmap In N,N-dimethyl-formamide	4.4-2 [4-2] Synthesis of 2-amino-N-(2,6-dioxopiperidin-3-yl)-6-methylbenzamide (Compound <4-3>) To the solution of 5-methyl-2H-benzo[d][1,3]oxazine-2,4[1 h]-dione (178 mg, 1.01 mmol) dissolved in DMF (4 ml), 3-aminopiperidine-2,6-dione (194 mg, 1.5 mmol) and DMAP (12 mg, 0.104 mmol) were added, and the mixture was heated at 60° C. overnight. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried on Na2SO4. The crude compound was obtained as a blue solid (50 mg), and this was used in the next step without further purification.

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - KR2020/24669, 2020, A Location in patent: Paragraph 0583; 0589-0590
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2020/62730, 2020, A1 Location in patent: Paragraph 0134; 0137

32
[ 116027-10-2 ]
[ 2353-44-8 ]
2-amino-N-(2,6-dioxopiperidin-3-yl)-5-iodobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In N,N-dimethyl-formamide at 60℃;	8.2 Step 2: Preparation of 2-amino-N-(2,6-dioxopiperidin-3-yl)-5-iodobenzamide 3-Aminopiperidine-2 in a solution of 6-iodo-2H-benzo [d] [1,3] oxazin-2,4 (1H) -dione (291mg, 1.01 mmol) dissolved in DMF (3ml), 6-Dione (129 mg, 1.01 mmol) and DMAP (12.3 mg, 0.101 mmol) were added and the mixture was warmed at 60 ° C. overnight. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried over Na2SO4. The crude compound was obtained as a blue solid (80 mg), which was used in the next step without further purification.
80 mg	With dmap In N,N-dimethyl-formamide	7.7-2 [7-2] Synthesis of 2-amino-N-(2,6-dioxopiperidin-3-yl)-5-iodobenzamide (Compound <7-3>) To the solution of 6-iodo-2H-benzo[d][1,3]oxazine-2,4(1H)-dione (291 mg, 1.01 mmol) dissolved in DMF (3 ml), 3-aminopiperidine-2,6-dione (129 mg, 1.01 mmol) and DMAP (12.3 mg, 0.101 mmol) were added, and the mixture was heated at 60° C. overnight. The reaction mixture was extracted with ethyl acetate, and the organic layer was dried on Na2SO4. The crude compound was obtained as a blue solid (80 mg), and this was used in the next step without further purification.

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY - KR2020/24669, 2020, A Location in patent: Paragraph 0622; 0628-0629
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2020/62730, 2020, A1 Location in patent: Paragraph 0152; 0155

33
[ 434-76-4 ]
[ 2353-44-8 ]
2-amino-N-(2,6-dioxopiperidin-3-yl)-6-fluorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		<strong>[434-76-4]2-Amino-6-fluorobenzoic acid</strong> (394 mg, 2.54 mmol) was dissolved in DMF (12 mL) and EDCl-HCl (540 mg, 2.8 mmol) and HOBt (429 mg, 2.8 mmol) were added. After stirring at room temperature for 30 minutes, amine (361 mg, 2.8 mmol) was added, DIPEA (1.4 mL, 8.12 mmol) was added and stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and purified by column chromatography to give 406 mg (60%) of pure 2-amino-N- (2,6-dioxopiperidin-3-yl) -6-fluorobenzamide compound as a white solid obtained.
60%		<strong>[434-76-4]2-amino-6-fluorobenzoic acid</strong> (394 mg, 2.54 mmol) was dissolved in DMF (12 ml) and EDCl-HCl (540 mg, 2.8 mmol) and HOBt (429 mg, 2.8 mmol) were added. After stirring at a room temperature for 30 minutes, amine (361 mg, 2.8 mmol) was added, and DIPEA (1.4 ml, 8.12 mmol) was added, and it was stirred at a room temperature for 16 hours. The reaction mixture was diluted with water and then was extracted with ethyl acetate. The organic layer was dried on Na2SO4, and it was purified by column chromatography, to obtain pure 2-amino-N-(2,6-dioxopiperidin-3-yl)-6-fluorobenzamide compound 406 mg (60%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 10.90 (s, 1H), 8.53 (d, J=6.0 Hz, 1H), 7.09 (dd, J=14.9, 8.1 Hz, 1H), 6.52 (d, J=8.2 Hz, 1H), 6.42-6.26 (m, 1H), 6.00 (s, 2H), 4.84-4.61 (m, 1H), 2.97-2.70 (m, 1H), 2.56-2.54 (m, 1H), 2.24-1.94 (m, 2H); MS found (M+H)+ (m/z), 266.09; calcd for C12H12FN3O3 m/z, 266.10.

Reference： [1]Patent: KR2020/24669,2020,A .Location in patent: Paragraph 0539; 0541-0543
[2]Patent: US2020/62730,2020,A1 .Location in patent: Paragraph 0104-0107

34
[ 2353-44-8 ]
[ 78471-43-9 ]
[ 1010100-26-1 ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;	1 Step 1: Preparation of 3-(5-bromo-1-oxoisoindolin-2-yl)piperidine-2,6-dione Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 4-bromo-2-(bromomethyl)benzoate (10.0 g, 32.47 mmol, 1.00 equiv) in N,N-dimethylformamide (30 mL), 3-aminopiperidine-2,6-dione (4.2 g, 32.78 mmol, 1.00 equiv), triethylamine (8.2 g, 81.04 mmol, 2.50 equiv). The resulting solution was stirred for 12 h at 80. The reaction was then quenched by the addition of water. The solid was collected, and the resulting solution was extracted with ethyl acetate and the organic layers combined. The resulting mixture was washed with brine. The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). The collected fractions were combined and concentrated under vacuum. This resulted in 5.6 g (53%) of 3-(5-bromo-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione as a purple solid. LC/MS (ESI) m/z: 323.00/325.00 [M+1] +.

Reference： [1]Current Patent Assignee: YALE UNIVERSITY; ARVINAS - WO2020/51564, 2020, A1 Location in patent: Paragraph 1863; 1864

35
[ 652-03-9 ]
[ 2353-44-8 ]
2-(2,6-dioxopiperidin-3-yl)-4,5,6,7-tetrafluoroisoindoline-1,3-dione, [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.92 g	In acetonitrile at 80℃; for 8h;	Preparation of compound 1: According to the molar ratio of 1:1.05, weigh 23.8g of tetrafluorophthalic acid and 13.44g of aminopiperidine-2,6-dione into the flask, add 150mL of acetonitrile,Place it in a 80°C oil bath with magnetic stirring and reflux for 8 hours. Then cool to room temperature,And cool down at -10°C to crystallize and filter, then the filter cake is vacuum dried,A total of 7.92 g of compound 1 is obtained, and the measured nuclear magnetic H spectrum and F spectrum are shown in Figure 1 and Figure 2, respectively.

Reference： [1]Current Patent Assignee: GUANGDONG HEC TECHNOLOGY HOLDING CO., LTD. - CN112358465, 2021, A Location in patent: Paragraph 0052-0053

36
[ 28418-88-4 ]
[ 2353-44-8 ]
[ 959150-64-2 ]

Yield	Reaction Conditions	Operation 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

37
[ 875895-67-3 ]
[ 2353-44-8 ]
[ 1416990-08-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 18h;	3.B General Procedure C: [0410] Compound 1 (1 mmol), DIPEA (2.1 mmol) and compound 2 hydrochloride (1.3 mmol) were dissolved in 5 ml DMF, the mixture was heated at 80oC for 18 hours (TLC and LCMS control). The reaction mixture was cooled, filtered and the solvent was evaporated. The crude residue was purified using HPLC. Yield: 49%.

Reference： [1]Current Patent Assignee: ORIONIS BIOSCIENCES NV - WO2021/126973, 2021, A1 Location in patent: Paragraph 0407; 0410; 0438; 0440

38
[ 131524-43-1 ]
[ 2353-44-8 ]
[ 1061604-41-8 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium tris(acetoxy)borohydride; acetic acid In methanol at 80℃; for 12h;	3.A General Procedure A: [0421] Compound 1 (1 mmol), NaH(OAc)3 (5 mmol), HOAc (1 mmol) and compound 2 (1.3 mmol) were dissolved in 5 ml of MeOH, the mixture was heated at 80oC for 12 hours. TLC and LCMS control. The reaction mixture was cooled, then filtered and the solvent was evaporated. The crude residue was purified using HPLC. Yield 58%.

Reference： [1]Current Patent Assignee: ORIONIS BIOSCIENCES NV - WO2021/126973, 2021, A1 Location in patent: Paragraph 0420; 0421

39
[ 2353-44-8 ]
[ 1312023-72-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: anhydrous Sodium acetate; acetic acid / 16 h / 100 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / acetonitrile / 4 h / 90 °C
	Multi-step reaction with 2 steps 1: anhydrous Sodium acetate; acetic acid / 6 h / 80 °C 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / Reflux

Reference： [1]Current Patent Assignee: CULLGEN SHANGHAI - WO2021/170109, 2021, A1
[2]Current Patent Assignee: J2H BIOTECH INC - KR2022/35014, 2022, A

40
[ 51108-29-3 ]
[ 2353-44-8 ]
2-(2,6-dioxopiperidin-3-yl)-4-fluoro-2,3-dihydro-1H-isoindole-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With anhydrous potassium acetate; acetic acid; for 8h;Reflux; Inert atmosphere;	To a stirred solution of 1 (4-fluoroisoindoline-1,3-dione) (10.0g, 60.6mmol) in acetic acid (100mL) was added with potassium acetate (7.1g, 72.7mmol) and 3-aminopiperidine-2,6-dione (5.2g, 40.4mmol). The mixture was heated to reflux and stirred for 8h and then cooled to room temperature. Water was added in the mixture and precipitation occurred. The solid was collected and dried after filtration to give the title compound (10g, 87% yield) as a gray solid. The product was directly used in the next step without further purification. 1H NMR (400MHz, Methanol-d4) δ 7.95-7.85 (m, 1H), 7.76 (d, J=7.3Hz, 1H), 7.58 (t, J=8.8Hz, 1H), 5.17 (dd, J=12.6, 5.5Hz, 1H), 2.96-2.84 (m, 1H), 2.82-2.67 (m, 2H), 2.22-2.12 (m, 1H). MS (ESI) 277.1 [M+H]+.
87%	With anhydrous potassium acetate; acetic acid; for 8h;Reflux; Inert atmosphere;	To a stirred solution of 1 (4-fluoroisoindoline-1,3-dione) (10.0g, 60.6mmol) in acetic acid (100mL) was added with potassium acetate (7.1g, 72.7mmol) and 3-aminopiperidine-2,6-dione (5.2g, 40.4mmol). The mixture was heated to reflux and stirred for 8h and then cooled to room temperature. Water was added in the mixture and precipitation occurred. The solid was collected and dried after filtration to give the title compound (10g, 87% yield) as a gray solid. The product was directly used in the next step without further purification. 1H NMR (400MHz, Methanol-d4) δ 7.95-7.85 (m, 1H), 7.76 (d, J=7.3Hz, 1H), 7.58 (t, J=8.8Hz, 1H), 5.17 (dd, J=12.6, 5.5Hz, 1H), 2.96-2.84 (m, 1H), 2.82-2.67 (m, 2H), 2.22-2.12 (m, 1H). MS (ESI) 277.1 [M+H]+.

Reference： [1]European Journal of Medicinal Chemistry,2022,vol. 236
[2]European Journal of Medicinal Chemistry,2022,vol. 236

41
[ 610-35-5 ]
[ 2353-44-8 ]
[ 64567-60-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With anhydrous Sodium acetate	1 Step 1: Step 1: Preparation of 2-(2,6-dioxopiperidin-3-yl)-5-hydroxyisoindoline-1,3-dione A solution of 3-aminopiperidine-2,6-dione (4.1 g, 24.7 mmol, 1.50 eq, HCl salt) in acetic acid (45 mL) was charged with sodium acetate (4.1 g, 49.4 mmol, 3.00 eq), then the mixture was stirred at 25° C. for 1 hour. Then 4-hydroxyphthalic acid (3.0 g, 16.5 mmol, 1.00 eq) was added into the mixture and heated to 120° C., stirred for additional 11 hours. The mixture was concentrated and then poured into water (20 mL), and then filtered. The crude product was purified by column chromatography (dichloromethane:methanol=50:1 to 10:1) to afford 2-(2,6-dioxo-3-piperidyl)-5-hydroxy-isoindoline-1,3-dione (3.9 g, 14.3 mmol, 86% yield) as a colorless solid. LC/MS (ESI) m/z: 275 [M+1]+; 1H-NMR (400 MHz, CDCl3) δ 11.19-10.94 (m, 2H), 7.75 (d, J=8.0 Hz, 1H), 7.20-7.08 (m, 2H), 5.08 (dd, J=5.2, 12.8 Hz, 1H), 3.34 (br s, 1H), 2.95-2.81 (m, 1H), 2.64-2.55 (m, 1H), 2.08-1.98 (m, 1H).

Reference： [1]Current Patent Assignee: ARVINAS - US2022/144809, 2022, A1

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Code	Phrase
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 2353-44-8 ] {[proInfo.proName]}

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[ 2353-44-8 ] Synthesis Path-Upstream 1~4

[ 2353-44-8 ] Synthesis Path-Downstream 1~41

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