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CAS No. : | 17702-83-9 | MDL No. : | MFCD00060523 |
Formula : | C16H20BrNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LAMUQORCSIHVMC-UHFFFAOYSA-N |
M.W : | 338.24 | Pubchem ID : | 253681 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 88.24 |
TPSA : | 37.38 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.98 cm/s |
Log Po/w (iLOGP) : | 3.42 |
Log Po/w (XLOGP3) : | 4.76 |
Log Po/w (WLOGP) : | 3.64 |
Log Po/w (MLOGP) : | 3.44 |
Log Po/w (SILICOS-IT) : | 4.5 |
Consensus Log Po/w : | 3.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.63 |
Solubility : | 0.00793 mg/ml ; 0.0000234 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.28 |
Solubility : | 0.00179 mg/ml ; 0.0000053 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.12 |
Solubility : | 0.000256 mg/ml ; 0.000000757 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.22 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
67% | In N-methyl-acetamide; | a) Preparation of 8-bromooctylphthalimide Potassium phthalimide (5.4 mmoles) was added to a solution of 1,8-dibromooctane (4.41 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80 C. approx. under stirring. Reaction times and process as per Example 4. 2.8 g of pure product were obtained. Yield 67%. Analysis: calcd.: C, 74.39; H, 7.80; N, 5.42. found: C, 74.54; H, 7.78; N, 5.08. |
67% | In N-methyl-acetamide; | a) Preparation of 8-bromooctylphthalimide Potassium phthalimide (5.4 mmoles) was added to a solution of 1,8-dibromooctane (4.41 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80C approx. under stirring. Reaction times and process as per Example 4. 2.8 g of pure product were obtained. Yield 67%. |
With potassium carbonate; In acetone; for 8h;Reflux; | General procedure: A 500 mL round-bottom flask was charged with4.63 g (0.025 mol) Phthalimide potassium salt, dissolve in 120 mL Anhydrousacetone. 6.9 g (0.05 mol) potassium carbonate and 11.75 g (0.0625 mol) 1,2-Dibromoethanewas added. The solution was heated to reflux for 8 h. The stirring mixture wasallowed to cool, and then was filtered. The solids were washed with 50 mL ofacetone, followed by 50 mL of EtOAc. The filtrate and the washer liquid werepooled and concentrated in a rotary evaporator, then purified by flashchromatography on SiO2 (gradient, 1:6 to 1:4 petroleum ether:EtOAc)to obtain 5.2 g (81.8%) of N-(2-Bromoethyl) phthalimideas a white solid. |
With potassium iodide; In acetone; for 10h;Reflux; | General procedure: To a solution of potassium 1,3-dioxoisoindolin-2-ide (1.85 g, 10.0 mmol), potassium iodide (0.08 g, 0.5 mmol) in acetone (25.0 mL), 1,2-dibromoethane dissolved in acetone (5.0 mL) was added by dropping funnel (3.72 g, 20.0 mmol), refluxed for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel to give the desired intermediate 4 2-(2-bromoethyl) isoindoline-1,3-dione (1.83 g, 72.5% yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium carbonate; In acetonitrile; for 20h;Reflux; | General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained. |
53% | In diethyl ether; | a) Preparation of 8-pyrrolidinyloctylphthalimide 8-Bromooctylphthalimide (517 mg; 2.0 mmoles) and pyrrolidine (0.33 ml; 4.0 mmoles) were dissolved in anhydrous ethyl ether (5 ml). Reaction times and process as per Example 1. 348 mg of pure product were obtained. Yield 53percent. Analysis: calcd.: C, 73.14; H, 8.59; N, 8.53. found: C, 73.11; H, 8.75; N, 8.54. |
53% | In diethyl ether; | a) Preparation of 8-pyrrolidinyloctylphthalimide 8-Bromooctylphthalimide (517 mg; 2.0 mmoles) and pyrrolidine (0.33 ml; 4.0 mmoles) were dissolved in anhydrous ethyl ether (5 ml). Reaction times and process as per Example 1. 348 mg of pure product were obtained. Yield 53percent. |
With potassium carbonate; In acetone; for 6h;Reflux; | General procedure: To asolution of intermediate 12 (2.0 mmol) andanhydrous K2CO3 (0.69 g, 5.0 mmol) in acetone (10 mL), pyrrolidine(2.5 mmol) was added. After reflux for 6 h until thestarting material 12 disappeared,the solvent was removed under vacuum, the residue was poured into water andextracted with EtOAc, the solution was dried over Na2SO4and then concentrated, the compounds 13 wereused without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54.8% | In acetonitrile; | a) Preparation of 8-(cis/trans-2,6-dimethyl)morpholinyloctyl phthalimide 8-Bromooctylphthalimide (9 g; 26.60 mmoles) and 2,6-dimethyl morpholine (cis-trans isomers mix) (9.8 ml; 79.5 mmoles) were dissolved in anhydrous acetonitrile (50 ml). The mixture was allowed to stir at room temperature for 18 hours approx. The reaction was discontinued by solvent evaporation under reduced pressure. The collected residue was purified by chromatography on silica gel (CH2 Cl2 /MeOH 95:5). The first product isolated (Rf =0.7) is a light yellow oil (A trans) (2.04 g), the second (Rf =0.4) is a yellow oil (B cis) (3.4 g). Total yield 54.8percent. Analysis: calcd.: C,70.93; H,8.66; N,7.52. Compound A (trans isomer) found: C,71.14; H,8.58; N,7.59. Compound B (cis isomer) found: C,71.07; H,8.53; N,7.65. |
54.8% | In acetonitrile; | a) Preparation of 8-(cis/trans-2,6-dimethyl)morpholinyloctyl phthalimide 8-Bromooctylphthalimide (9 g; 26.60 mmoles) and 2,6-dimethyl morpholine (cis-trans isomers mix) (9.8 ml; 79.5 mmoles) were dissolved in anhydrous acetonitrile (50 ml). The mixture was allowed to stir at room temperature for 18 hours approx. The reaction was discontinued by solvent evaporation under reduced pressure. The collected residue was purified by chromatography on silica gel (CH2Cl2/MeOH 95:5). The first product isolated (Rf = 0.7) is a light yellow oil (A trans) (2.04 g), the second (Rf = 0.4) is a yellow oil (B cis) (3.4 g). Total yield 54.8percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Using the same procedure, <strong>[17702-83-9]N-(8-bromooctyl)phthalimide</strong> was converted to 2-[8-(1H-imidazol-1-yl)octyl]-1H-isoindole-1,3(2H)-dione, mp 43°-45° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In acetonitrile; | b) Preparation of 8-morpholinyloctylphthalimide 8-Bromooctylphthalimide (676 mg; 2.0 mmoles) and morpholine (0.35 ml; 4.0 mmoles) were dissolved in anhydrous acetonitrile (5 ml). Reaction times and process as per Example 1. 331 mg of pure product were obtained. Yield 48percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In diethyl ether; | a) Preparation of 8-piperidinyloctylphthalimide 8-Bromooctylphthalimide (517 mg; 2.0 mmoles) and piperazine (0.40 ml; 4.0 mmoles) were dissolved in anhydrous ethyl ether (5 ml). Reaction times and process as per Example 1. 431 mg of pure product were obtained. Yield 63percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With hydrazine hydrate; In methanol; dichloromethane; acetonitrile; | step 1 8-Morpholin-4-yloctylamine To a solution of <strong>[17702-83-9]N-(8-bromooctyl)phthalimide</strong> (8.46 g, 25.0 mmol) in CH3CN (70 mL) at room temperature wag added morpholine (4.80 g, 55.0 mmol). After 18 h at this temperature, the reaction mixture was concentrated and then diluted with EtOAc (100 mL). The organic layer was washed with 10percent aq. Na2CO3 (3*30 mL), H2O (2*20 mL), and brine (2*20 mL) and then dried (Na2SO4). After concentration, the residue was purified by the flash chromatography (5 to 10percent MeOH/CH2Cl2 gradient) to afford the substituted morpholine intermediate. To this substituted morpholine intermediate (7.40 g, 21.5 mmol) in MeOH (70 mL) at room temperature was added hydrazine monohydrate (1.28 mL, 25.8 mmol) and the resulting mixture was heated to reflux. After 2 h at this temperature, the reaction was concentrated and then diluted with 1N HCl (100 mL). The mixture was stirred for 1 h, and the precipitate that formed during this time was filtered and washed with excess 0.5 N HCl. The filtrate was basified with 50percent aq. NaOH (~7 mL) and stirred about 15 min. This aqueous solution was extracted with CHCl3 (4*50 mL) and the combined organic layers were washed with H2O (3*50 mL) and brine (1*50 mL). The organic layer was then dried (Na2SO4) and concentrated to afford the product (4.16 g, 77percent) as an oil; 1H NMR (DMSO-d6) delta81.18-1.34 (m, 12H), 1.34-1.43 (m, 2H), 2.21 (t, J=7.0 Hz, 2H), 2.26-2.33 (m, 4H), 2.46-2.52 (m, 2H), 3.53 (t, J=4.6 Hz, 4H); IR (film) 3390, 2930, 2860, 2820, 2790, 2710, 2180, 1640, 1610, 1460, 1390, 1375, 1360, 1320, 1300, 1275, 1200, 1135, 1120, 1080, 1040, 1010, 900, 870, 815, 800, and 725 cm-1; mass spectrum [(+) APCI], m/z 215 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With sodium hydrogencarbonate; potassium carbonate; hydrazine hydrate; In methanol; ethyl acetate; Petroleum ether; | step 1 8-(Benzoxazol-2-ylsulfanyl)-octylamine To a round bottom flask with 2-mercaptobenzoxazole (2.14 g, 14.2 mmol) andDMF (100 mL) at room temperature was added K2CO3 (2.61 g, 18.9 mmol) followed by <strong>[17702-83-9]N-(8-bromooctyl)phthalimide</strong> (4.00 g, 11.8 mmol). The resulting solution was heated to 60° C. for 0.5 h and then cooled back to room temperature. At this point, the reaction mixture was quenched with H2O (100 mL) and then diluted with EtOAc (600 mL). The organic layer was washed with 1 N HCl (60 mL), sat. aq. NaHCO3 (60 mL), and brine (60 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20percent EtOAc/petroleum ether gradient) to afford the thioether intermediate. To this thioether intermediate (3.02 g, 7.39 mmol) in MeOH (40 mL) at room temperature was added hydrazine monohydrate (0.860 mL, 17.7 mmol) and the resulting mixture was heated to reflux. After 18 h at this temperature, the reaction was concentrated, taken up in EtOAc (300 mL), and filtered to remove insoluble materials. This phthalimide byproduct was washed with excess EtAOc, and the filtrate was washed with H2O (40 mL) and brine (40 mL). The organic layer was then dried (Na2SO4) and concentrated to afford the product (1.87 g, 57percent) as an oil; 1H NMR (CDCl3) delta1.14-1.67 (m, 12H), 1.72-1.92 (m, 2H), 2.69 (t, J=9.6 Hz, 2H), 3.32 (t, J=8.5 Hz, 2H), 7.16-7.34 (m, 2H), 7.38-7.47 (m, 1H), 7.54-7.66 (m, 1H); mass spectrum [(+) ESI], m/z 279(M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In acetonitrile; for 48h;Reflux; | A mixture of compound 54 (0.85 g, 5.62 mmol), Na2CO3 (0.95 g, 8.99 mmol), and compound 3 (2.16 g, 6.39 mmol) in CH3CN (40 ml) was sirred under reflux for 48 h, cooled, and poured onto ice-water (300 ml). The mixture was extracted with CH2CI2 (3 x 100 ml), the combined extracts were dried (Na2SO4), and concentrated. The residue was purified by column chromatography (petroleum ether-EtOAc (5: 1)) to afford a 2: 1 mixture of the title compound 55 with the starting amine 54 as a colourless oil which was used in the next step without further purification. 1H-NMR (200 MHz, CDCI3, HMDSO): delta 1.15 (t, J=7.1 Hz, 3H); 1.22-1.41 (m, 8H); 1.47-1.76 (m, 4H); 2.74 (q, 3=1.1 Hz, 2H); 3.67 (t, 3=1.1 Hz, 2H); 4.69 (s, 2H); 7.23-7.39 (m, 5H), 7.64-7.75 (m, 2H); 7.78-7.88 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20℃; for 2.5h; | To a solution of a phtalimide protected aminalkanol (1 eq) in CH3CN (3 imL/mmol) was added PPh3 (1 eq) and CBr4 (1 eq) and the mixture was stirred at rt for IVi h. The reaction mixture was concentrated and purified by chromatography (mixtures of petroleum ether and EtOAc) to afford the corresponding alkylbromide (VIII).; General procedure 2. Starting material: compound 2. 1H-NMR (DMSO-^6): delta 7.89-7.82 (m, 4H), 3.58-3.49 (m, 4H), 1.81-1.72 (m, 2H), 1.63-1.54 (m, 2H), 1.40-1.23 (m, 8H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 3h;Microwaves; | A solution of an alkylbromide of general formula (VIII) (1 eq) in dry DMF (0.5 mL/mmol) was added to a flask suited for microwave heating. The amine (VII) (1 eq) was dissolved in DMF and added to the reaction flask and then K2CO3 (3 eq) was added. The reaction mixture was heated in a microwave oven at 7O0C for 3 h. The reaction was quenched with water, extracted with EtOAc and the organic phase concentrated to dryness, purified by chromatography using appropriate mixture of MeOH/CHCI3/NH3 to afford protected amines of general formula (IX).; Preparation 6: 2-(8-(cvclohexyl(3-morpholinopropyl)amino)octyl)isoindoline-l,3-dione (compound 6). General procedure 3. Starting materials: compounds 1 and 3. 1H-NMR (DMSOd6): delta 7.89-7.82 (m, 4H), 3.58-3.52 (m, 6H), 2.39-2.21 (m, HH), 1.71-1.08 (m, 24H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.7% | In ethanol; for 12h;Reflux; | General procedure: To a solution of compound 5 (0.21 g, 10 mmol) in ethanol (20.0 ml), N-(3-bromopropyl)phthalimide (0.27 g, 10 mmol) was added, and the mixture was refluxed for 12 h. The reaction mixture was filtered to remove precipitated solid and the filtrate was concentrated under vacuum. The viscous residue was dissolved with 20 ml of ether, then washed with water and the ether layer was dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, the crude compound was chromatographed on silica gel to give O,O-diethyl-S-3-phthalimidopropyl phosphorothioate (0.12 g, 33.6percent yield) as light yellow oil. |
Tags: 17702-83-9 synthesis path| 17702-83-9 SDS| 17702-83-9 COA| 17702-83-9 purity| 17702-83-9 application| 17702-83-9 NMR| 17702-83-9 COA| 17702-83-9 structure
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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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