Structure of 24666-56-6
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CAS No. : | 24666-56-6 |
Formula : | C5H9ClN2O2 |
M.W : | 164.59 |
SMILES Code : | O=C(C(N)CC1)NC1=O.[H]Cl |
MDL No. : | MFCD11042437 |
InChI Key : | YCPULGHBTPQLRH-UHFFFAOYSA-N |
Pubchem ID : | 134548 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.6 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 40.82 |
TPSA ? Topological Polar Surface Area: Calculated from | 72.19 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | -0.69 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | -0.83 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | -0.55 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.19 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | -0.45 |
Log S (ESOL):? ESOL: Topological method implemented from | -0.43 |
Solubility | 61.8 mg/ml ; 0.375 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -0.35 |
Solubility | 73.3 mg/ml ; 0.445 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -0.47 |
Solubility | 55.9 mg/ml ; 0.34 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.79 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.71 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With triethylamine; In N,N-dimethyl-formamide; at 75℃; for 12h; | To a solution of 3-aminopiperidine-2,6-dione (2.00 g, 12.2 mmol, HCl) and <strong>[133446-99-8]methyl 2-(bromomethyl)-4-nitro-benzoate</strong> (4.21 g, 15.4 mmol) in DMF (10.0 mL) was added TEA (3.07 g, 30.4 mmol). The reaction mixture was stirred at 75 C. for 12 hrs. On completion, the reaction mixture was diluted with water (200 mL), filtered. The filtered cake was collected. The reaction mixture was concentrated in vacuo. The residue was triturated EA:H2O=1:1 (50 mL) to give the title compound (1.7 g, 48% yield) as a blue solid. 1H NMR (400 MHz, DMSO-d6) delta 11.04 (s, 1H), 8.53 (d, J=1.2 Hz, 1H), 8.36 (dd, J=2.0, 8.4 Hz, 1H), 7.98 (d, J=8.4 Hz, 1H), 5.17 (dd, J=5.2, 13.2 Hz, 1H), 4.69-4.45 (m, 1H), 3.01-2.86 (m, 1H), 2.68-2.59 (m, 1H), 2.48-2.35 (m, 1H), 2.13-2.02 (m, 1H). |
1.50 g | With potassium carbonate; In N,N-dimethyl-formamide; at 25 - 45℃; for 6h; | Preparation of <strong>[133446-99-8]methyl <strong>[133446-99-8]2-(bromomethyl)-4-nitrobenzoate</strong></strong> (23-1) (2.5 g, 9.12 mmol) and 3- aminopiperidine-2,6-dione (1-2) (1.74 g, 13.6 mmol) were added to DMF (12.5 ml) at 25C. Potassium carbonate (3.15 g, 22.8 mmol) was added to the reaction mixture at 25C and the temperature was raised to 42C. The reaction mixture was stirred for 6 hours at 42C and cooled to 20C to 25C. De-ionized water (12.5 ml) was added to the reaction mixture at 20C and stirred for 20 minutes. The solid obtained was filtered, washed with de-ionized water (2 x 25 ml) and dried under vacuum at 40C to 45C for 20 hours to obtain the title compound.Then the crude material was slurried with PE/EA(1/1) 20 mL to give 3-(5-nitro-1-oxoisoindolin-2-yl)piperidine- 2,6-dione (23-2) (1.50 g, 5.18 mmol, ) as gray-green solid. LC/MS (ES+): m/z 290 [M + H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Example 14; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 14 was prepared similarly according to the procedure for Example 13 except that there was no acetic acid; the amount of triethylamine was reduced from 4.6 mol to 3.2 mol; and the refluxing time was increased from about 5 to 7 hours to about 47 hours. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 94percent. | |
92% | Example 15; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 15 was prepared similarly according to the procedure for Example 13 except that there was no acetic acid and the 4.6 mol of triethylamine was replaced with 9.2 mole of imidazole. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 92percent | |
85% | Example 16; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 16 was prepared similarly according to the procedure for Example 13 except that the 4.6 mol of triethylamine was replaced with 9.2 mole of imidazole. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 85percent. |
84% | Example 13; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; According to Scheme E A mixture of <strong>[6946-22-1]<strong>[6946-22-1]3-aminophthalic acid</strong> hydrochloride</strong> (200 g, 0.92 mol, from Prosynth Ltd., Suffolk, UK), 3-aminoglutarimide hydrochloride (159 g, 0.96 mol, from Evotec OAI, Hamburg, Germany), acetonitrile (2.0 L), and acetic acid (577 g, 9.6 mol, from Fisher Scientifc) was charged into a reaction vessel. After the mixture was stirred for 15 minutes, triethylamine (465.0 g, 4.6 mol, from Aldrich, Milwaukee, Wis.) was added dropwise over 30-35 minutes while the reaction temperature was maintained at 20-25° C. Next, the reaction mixture was stirred further for 10-15 minutes and then refluxed at about 85 to 87° C. for about 5 to 7 hours or until the in-process control, i.e., HPLC AP at 240 nm, indicates that <2percent of the <strong>[6946-22-1]3-aminophthalic acid</strong> remained in the reaction mixture. After the reaction mixture was cooled to about 20 to 25° C. over 1-2 hours, 1.0 L of water was charged over 15-30 minutes at about 20 to 25° C. The resulting mixture was stirred at about 15 to 20° C. for about 20 to 30 minutes to provide a yellow solid precipitate, which was filtered, washed with DI water (3.x.1.0 L) and acetonitrile (2.x.500 mL), and then dried at about 35 to 40° C in vacuo to a constant weight at 210.0 g (84 percent). | |
68.5% | With acetic acid; triethylamine; In acetone; at 80 - 85℃; for 6h; | Acetonitrile (100 mL), acetic acid (26.28 mL, 459.5 mmol),Triethylamine (31.85 mL, 229.8 mmol), <strong>[6946-22-1]<strong>[6946-22-1]3-aminophthalic acid</strong> hydrochloride</strong> (10 g, 46.0 mmol),Aminopiperidine-2,6-dione hydrochloride (7.68 g, 46.6 mmol)Added to the reaction flask, heated to 80 ~ 85 ° C reflux, the reaction was complete after 6h,The reaction solution was cooled to 20 ~ 25 ° C, purified water was slowly added, the crystallization was stirred for 2h, filtered, the filter cake was dried under reduced pressure at 60 ± 5 ° C for 8h to obtain 8.6g black solid, yield 68.5percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Triethylamine (0.65 mi, 4.54 mmol) was added to a suspension of 16 (0.37 g, 2.27 mmol) in dry tetrahydrofuran (40 ml) and the mixture was stirred at room temperature for 10 min. Tetrafluorophthalic anhydride (17) (0.50 g, 2.27 mmol) was added and stirring was continued at room temperature for 48 h. The reaction mixture was partitioned between ethyl acetate and water and the aqueous portion was acidified with 2N HCl and extracted with ethyl acetate (5 times). The combined extracts were worked up to give an oil which was dried well in vacuo and then triturated with diethyl ether until crystallization began. The solid was filtered off and further triturated with cold diethyl ether (5 times) to give the title compound 2 as a white powder (0.54 g, 62%), mp 254-258 0C. 1H NMR (400 MHz, DMSO-D6) δ ppm 14.00 (br, IH), 10.85 (s, IH, exch. with D2O), 9.08 (d, J=8.0 Hz, IH, exch. with D2O), 4.75-4.69 (m, IH), 2.79-2.69 (m, <n="15"/>IH), 2.58-2.48 (m, IH), 2.08-2.00 (m, IH)5 1.99-1.90 (m, IH). Found: C, 44.71; H, 2.43; N3 7.82. C13H8F4N2O5 requires C, 44.84; H, 2.32; N, 8.05%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at 20.0℃; for 24.0h;Inert atmosphere; | Step 3. Synthesis of rac-2-Acetamido-N-(2,6-dioxopiperidin-3-yi)-6-nitrobenzamide [00302] The starting acid (3.10 g, 13.8 mmol) was mixed with hydroxybenzotriazole (HOBt, 2.12 g of the hydrate, 13.8 mmol) and l-ethyl-3-(3-dimethylaminopropyl)- carbodiimide hydrochloride (EDC, 2.54 g, 13.3 mmol), under a nitrogen atmosphere. N,N- dimethylformamide (DMF, 21.4 mL) was added and the mixture was stirred for 30 minutes at room temperature. rac-3-Aminopiperidine-2,6-dione hydrochloride (5.01 g, 30.4 mmol) was added, followed by Nu,Nu-diisopropylethylamine (DIEA, 9.63 mL, 55.3 mmol). The reaction mixture was stirred at 20C, while monitoring by HPLC. After 24 hours, the reaction mixture showed approximately 40% conversion to the desired product containing some remaining starting acid, but no amine. Then, the reaction mixture was slowly poured into 200 mL water with vigorous stirring. After 20 minutes, a white precipitate began to form. The mixture was placed in the refrigerator for 18 hours. Then, the precipitate was isolated by filtration. The filter cake was washed with 50 mL ether, and air dried to provide the title compound (1.60 g, 4.79 mmol, 35%) as a white powder. XH NMR (300 MHz, DMSO-d6) delta 1 1.16 (s, 1H), 9.40 (s, 1H), 9.34 (d, J = 8.0 Hz, 1H), 8.53 (d, J = 7.5 Hz, 1H), 7.89 (dd, J = 8.2, 0.98 Hz, 1H), 7.66 (t, J = 8.3 Hz, 1H), 4.79 (m, 1H), 2.85(m, 1H), 2.59 (m, 1H), 2.21 (m, 1H), 2.20 (s, 3H), 2.03 (m, 1H). MS (ESI-) calc. for [Ci4H14N406-H]" 333.3, found 333.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium acetate; acetic acid; at 120℃; for 16h; | 3,6-Difluorophthalic anhydride (77.3 mg, 0.40 mmol, 1.0 eq.), potassium acetate (120.8 mg, 1.24 mmol, 3.1 eq.), and 3-aminopiperidine-2,6-dione hydrochloride (80.4 mg, 0.48 mmol, 1.2 eq.) were dissolved in glacial acetic acid (1.2 mL, 0.33 M), and then the mixture was heated to 120 C. After 16 hours, the reaction was cooled to room temperature and the excess acetic acid was removed by rotary evaporation. The residue was dissolved in EtOAc and water (20 mL each), and the aqueous layer was extracted 4 times with EtOAc (15 mL). The combined organic layers were washed with water and then brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide the desired product as a tan solid (94.0 mg, 80% yield). NMR: (500 MHz, DMSO-i) delta 11.14 (s, 1H), 7.79 (t, J= 5.7 Hz, 2H), 5.15 (dd, J = 12.9, 5.4 Hz, 1H), 2.88 (ddd, J = 17.1, 13.8, 5.5 Hz, 1H), 2.60 (d, J = 17.3 Hz, 1H), 2.55 - 2.45 (m, 1H), 2.05 (m, 1H).MS: 295.17 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | [0132] To a solution of 3 -amino-2, 6-piperidinedi one HC1 (648 mg, 3.94 mmol) in DMF (20 mL) at RT was added TEA (1.21 mL, 8.67 mmol) and stirred for 10 min. The mixture was cooled to 0 C then a solution of <strong>[165111-46-6]methyl 2-(bromomethyl)-4-cyanobenzoate</strong> (1.00 g, 3.94 mmol) in DMF was added dropwise. After 10 min, the reaction was warmed to RT and stirred for 2 days then concentrated. The residue was purified by silica gel chromatography eluting with hexanes/EA (1 : 1) to hexanes (100%) to give 2-(2,6-dioxo-3-piperidyl)-l-oxo-5- isoindolinecarbonitrile (230 mg, 22% yield) as a solid. LCMS (ESI) m/z 270 [M+H] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With sodium acetate; acetic acid; for 3h;Reflux; | To a round bottom flask was added tetrafluorophthalic anhydride (1.65 g, 7.5 mmol) and 3-aminopiperidine-2,6-dione hydrochloride (0.82 g, 5.0 mmol). A solution of sodium acetate (0.5 g, 6.0 mmol) in glacial acetic acid (20 mL) was added and the colorless solution was refluxed for 3 h. After cooling, the purple suspension was filtered, and H2O (50 mL) was added to the filtrate. The colorless solid formed was collected, washed with H2O (3×5 mL) and petroleum ether (3×5 mL) and it was further dried in vacuo to give the title product as a colorless solid. Yield (1.13g, 68%); mp 238-240 C; 1H NMR (500 MHz, DMSO-d6) δ 2.01-2.11 (m, 1H), 2.41-2.65 (m, 2H), 2.82-2.93 (m, 1H), 5.18 (dd, J=5.4, 13.0Hz, 1H), 11.15 (br s, 1H); 13C NMR (126 MHz, DMSO-d6) δ 21.78, 30.95, 49.69, 113.52 (d, 3J (C,F)=8.3 Hz), 142.72 (m, 1J (C,F)=266Hz), 145.14 (m, 1J (C,F)=264Hz); 161.98, 169.31, 172.68; LC-MS (ESI) 99% purity, m/z [M+NH4]+ calcd for C13H6F4N2O4, 348.06; found, 348.1; HRMS m/z [M - H]- calcd for C13H6F4N2O4, 329.0191; found, 329.0201. |
Tags: 24666-56-6 synthesis path| 24666-56-6 SDS| 24666-56-6 COA| 24666-56-6 purity| 24666-56-6 application| 24666-56-6 NMR| 24666-56-6 COA| 24666-56-6 structure
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P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
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 |
Sorry,this product has been discontinued.
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