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CAS No. : | 145369-94-4 | MDL No. : | MFCD00272435 |
Formula : | C9H6BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 224.05 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.27 |
TPSA : | 32.86 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.77 cm/s |
Log Po/w (iLOGP) : | 1.79 |
Log Po/w (XLOGP3) : | 1.27 |
Log Po/w (WLOGP) : | 2.29 |
Log Po/w (MLOGP) : | 1.56 |
Log Po/w (SILICOS-IT) : | 3.26 |
Consensus Log Po/w : | 2.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.65 |
Solubility : | 0.506 mg/ml ; 0.00226 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.56 |
Solubility : | 6.18 mg/ml ; 0.0276 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -4.47 |
Solubility : | 0.00764 mg/ml ; 0.0000341 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.56 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
87% | at 0 - 188℃; for 6.5 h; | A mixture of 5-(((4-bromophenyl)amino )methylene)-2,2-dimethyl-1 ,3-dioxane-4, 6-dione (50 g, 154 mmol) in 1,2-dichlorobenzene (500 mL) was stirred at 188°C for 3.5 h. Thereaction was then cooled down to 0°C and stirred further for 3 h. The solid was collected byfiltration, and was then washed with methyl tert-butyl ether (100 mL) to give the title compoundas a brown solid (30.6 g, 87percent). The title compound was characterized by LC-MS and 1H NMRas shown below:LC-MS (ESI, pos. ion) m/z: 224 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 6.32 (d, J= 7.32 Hz, 1H), 7.48 (d, J= 9.08 Hz, 1H), 7.77(dd, J= 8.88 Hz, 2.32 Hz, 1H), 7.95 (d, J = 7.32 Hz, 1H), 8.34 (d, J = 2.28 Hz, 1H). |
87% | at 188℃; for 3.5 h; | The 5 - (( (4-bromophenyl) amino) methylene) - 2,2-dimethyl -1,3-dioxane -4,6-dione (50g, 154mmol) in 1,2-dichlorobenzene (500 ml) solution is heated to 188 °C, stirring for 3.5 hours, cooling to 0 °C, continue to stir 3 hours. Filtering, collecting solid, solid after armoruncle ether (100 ml) eluting, to obtain the title compound as brown solid (30.6g, 87percent). |
29.9 g | at 190℃; for 0.25 h; | Diphenyl ether (519.9 g, 3.064 mol)Add to a 1000 mL three-necked flask,Preheat to 190 ° C,Compound 2a (50.1 g, 0.153 mol) was added slowly,Reaction for 15 min.TLC detection [V (dichloromethane): V (methanol) = 15:1] reaction junctionbundle,cool down,The reaction solution was poured into 600 mL of petroleum ether and stirred.Precipitating solids,Filtering,dry,Made a grayish yellow solid 29.9g, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | for 9 h; Heating / reflux | The solid 6-bromo-4-hydroxy-quinoline-3-carboxylic acid (102.59 g, 337.7 mmol) was added to hot diphenyl ether (508 g) and then the mixture was heated to reflux for 9 h to afford a light brown suspension. After cooling to room temperature, the mixture was diluted with methanol (20 mL) and diethyl ether (300 mL). Then, the solids were collected by filtration and washed with diethyl ether. After drying in air, 72.43 g (95percent yield) of 6-bromo-quinolin-4-ol was isolated as a white solid: EI-HRMS m/e calcd for C9H6BrNO (M+) 222.9633, found 222.9630. |
90% | for 0.5 h; Reflux | . Deprotection and removal of the carboxylic acid |
90% | for 0.5 h; Reflux | 10558] The bicyclic compound 3-2 is prepared from bromoaniline 3-1 using diethyl 2-(ethoxymethylene)malonate or a similar reagent. Deprotection and removal of the carboxylic acid, followed by halogenation using a reagent such as phosphorus oxychloride yields compound 3-5. Derivatization with pyridine boronate in Suzuki coupling conditions yields 3-6, which is reacted in a second Suzuki reaction with a benzothiazolyl boronate to yield compound 3-7. Subsequent heating in hydrochloric acid in a solvent such as methanol results in removal of an acetyl group. |
77% | at 260℃; for 2 h; | 4.1.7 6-Bromoquinolin-4-ol (10) 6-Bromo-4-hydroxyquinoline-3-carboxylic acid (9) (5.0 g, 18.73 mmol) was added to a 100 mL round-bottomed flask in Ph2O (30 mL) and then stirred at 260 °C for 2 h. After cooling to 60 °C, 30 mL petroleum ether was added and the suspended solid was filtered, washed with petroleum ether, EtOAc and dried under reduced pressure to give the title compound (3.21 g, 14.39 mmol, 77percent yield) as a brown solid. ESI-MS: m/z = 224 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: With sulfuric acid In acetonitrile for 0.333333 h; Stage #2: With potassium permanganate In acetonitrile at 85℃; for 5 h; |
Add 6-bromo-4-oxo-2,3-dihydroquinoline (0.01 mol) to a 25 ml reaction flask, add 15 ml of acetonitrile, concentrated sulfuric acid (0.02 mol), stir for 20 minutes, and slowly add potassium permanganate. (0.02 mol), the reaction was stirred at 85 ° C, the progress of the reaction was monitored by TLC, and the reaction was stopped after 5 hours. After the reaction solution is cooled to room temperature, it is poured into 50 ml of water, stirred and filtered to obtain a crude product of 6-bromo-4-hydroxyquinoline, which is separated by silica gel column chromatography (column chromatography silica gel 100-200 mesh, eluent oil) Ether: ethyl acetate = 1:4). The eluent was concentrated to give the product. The yield was 86percent, and the purity was 96percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.5% | at 220℃; for 0.0833333 h; | Compound 1g (47.9 mmol, 10 g) was dissolved in diphenyl oxide and heated to 220 ℃ for 5 min. After cooling, the precipitated solid was filtered and washed with petroleum ether. Yield 83.5percent. HPLC purity: 96.7percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.5% | for 6 h; Heating / reflux | The solid 6-bromo-quinolin-4-ol (52 g, 232.1 mmol) was added to phosphorus oxychloride (213.5 mL) and then the mixture was heated to reflux for 6 h to afford a light brown solution. After cooling to room temperature, the excess phosphorus oxychloride was removed under the vacuum. The remaining residue was poured into an ice-containing beaker (2 L). Then, it was slowly neutralized with solid potassium carbonate and the resulting solids were collected by filtration and washed with water. After drying in air, 55.46 g (98.5percent yield) of 6-bromo-4-chloro-quinoline was isolated as a light yellow solid: EI-HRMS m/e calcd for C9H5BrClN (M+) 240.9294, found 240.9297. |
93% | for 1.5 h; Reflux | 10558] The bicyclic compound 3-2 is prepared from bromoaniline 3-1 using diethyl 2-(ethoxymethylene)malonate or a similar reagent. Deprotection and removal of the carboxylic acid, followed by halogenation using a reagent such as phosphorus oxychloride yields compound 3-5. Derivatization with pyridine boronate in Suzuki coupling conditions yields 3-6, which is reacted in a second Suzuki reaction with a benzothiazolyl boronate to yield compound 3-7. Subsequent heating in hydrochloric acid in a solvent such as methanol results in removal of an acetyl group. |
84% | With trichlorophosphate In N,N-dimethyl-formamide at 120℃; for 5 h; | 4.1.8 6-Bromo-4-chloroquinoline (11) To a 100 mL round-bottomed flask was added 6-bromoquinolin-4-ol (10) (3.0 g, 13.45 mmol), POCl3 (20 mL) and DMF (0.5 mL). The mixture was stirred at reflux for 6 h. After cooling to room temperature, the reaction mixture was poured into ice water (100 mL) and stirred for 1 h. Then the pH of the mixture was adjusted to 8 using saturated aqueous NaHCO3. The mixture was extracted with EtOAc and the organic phase was dried over sodium sulfate and concentrated in vacuo to give the title compound (2.75 g, 11.36 mmol, 84percent yield) as a white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.87 (d, J = 4.5 Hz, 1H, Ar-H), 8.32 (d, J = 2.0 Hz, 1H, Ar-H), 8.03 (d, J = 9.0 Hz, 1H, Ar-H), 7.99 (dd, J = 9.0, 2.0 Hz, 1H, Ar-H), 7.82 (d, J = 4.5 Hz, 1H, Ar-H). ESI-MS: m/z = 242 [M+H]+. |
84% | Stage #1: Heating / reflux |
6-Bromo-4-chloroquinoline. The solution of the compound from Example 17b (2 g, 8.9 mmol) in POCI3 (10 mL) was refluxed overnight, cooled and quenched by ice water. The precipitate was collected, washed with H2O and dried in vacuo to afford the title compound as a grey solid (1.8 g, 84percent). 1 H NMR (400 MHz, DMSO-CZ6) δ ppm 8.90 (d, J=4.80 Hz, 1 H) 8.37 (d, J=2.02 Hz, 1 H) 8.07 (d, J=8.59 Hz, 1 H) 8.03 (dd, J=8.84, 2.02 Hz, 1 H) 7.86 (d, J=4.55 Hz, 1 H). |
32% | With trichlorophosphate In toluene at 115℃; for 4 h; | To a suspension of 6-bromo-4-hydroxyquinolin (14.55 g, 64.9 mmol) in toluene (20mL) was added POCh (6.05 mL, 64.9 mmol) slowly. The reaction was stirred at 115°C for 4 h,then cooled down to 0°C and diluted with DCM (400 mL). The mixture was washed with 4MNaOH (70 mL) followed by brine (100 mL), dried over anhydrous Na2S04 and concentrated invacuo. The residue was recrystallized in n-heptane (150 mL) to give the title compound as ayellow solid (5.5 g, 32percent). The title compound was characterized by LC-MS and 1H NMR asshown below:LC-MS (ESI, pos. ion) m/z: 242 [M+Ht;1H NMR (400 MHz, CDCh) 8 (ppm): 7.50 (d, J= 4.72 Hz, 1H), 7.82 (dd, J= 8.96 Hz, 2.16 Hz,1H), 7.98 (d, J= 8.92 Hz, 1H), 7.95 (d, J= 2.16 Hz, 1H), 8.34 (d, J= 4.68 Hz, 1H). |
32% | With trichlorophosphate In toluene at 115℃; for 4 h; | To 6-bromo-4-hydroxyquinoline (14.55g, 64 . 9mmol) toluene (20 ml) is slowly added in solution POCl 3 (6.05 ml, 64 . 9mmol). responds the fluid in 115 °C stirring 4 hours, cooling to 0 °C, and added DCM (400 ml) dilution. The resulting mixed solution for sequentially 4MNaOH aqueous solution (70 ml) and the brine (100 ml) washing, anhydrous Na 2 SO 4 drying, and concentrated under reduced pressure. In normal heptane of the residue (150 ml) is recrystallized in, to obtain the title compound as yellow solid (5.5g, 32percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.6% | With phosphorus trichloride In toluene for 2 h; Reflux | willL0g (44.63 mol) of 6-bromoquinolin-4 (1H) -one, 100 ml of toluene and 12.25 g (89.26 mol) of phosphorus trichloride were added to a 250 ml three-necked flask and heated to reflux for 2 hours. , Dried and dried. The solid was beaten with ether (100 ml), filtered and dried to give a yellow powder (yield 92.6percent). |
85% | for 3 h; Heating / reflux | Diphenyl ether (80 ml) was added to 4-bromoaniline (4.5 g) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxan-4,6-dione (5.4 g), and the mixture was stirred at 80°C for one hr. Biphenyl (24.2 g) was added thereto, and the mixture was stirred at 220°C for 3 hr. The reaction mixture was cooled to room temperature, and diethyl ether was added to the cooled mixture. The precipitated crystal was collected by filtration and was washed with diethyl ether. The residue was purified by column chromatography with a hexane-acetone system to give 6-bromoquinolone (1.57 g, yield 27percent). Thionyl chloride (5 ml) and a minor amount of dimethylformamide were added to 6-bromoquinolone (1.6 g), and the mixture was stirred under reflux for 3 hr. The reaction mixture was added to a saturated aqueous sodium bicarbonate solution under ice cooling, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with a hexane-ethyl acetate system to give 6-bromo-4-chloroquinoline (1.43 g, yield 85percent). |
70% | With trichlorophosphate In N,N-dimethyl-formamide for 2 h; Reflux | A mixture of 4 (17.0 g, 131.5 mmol), POCl3 (180 mL) and anhydrous DMF (18 mL) was stirred and heated at reflux for 2 h. After removal of POCl3, the residue was poured into ice water and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (4:1 hexanes/EtOAc) to afford 5 (12.8 g, 70percent) as a white solid, mp 111-112 °C (lit31 111-112 °C). 1H NMR (CDCl3) δ 8.79 (d, J = 5.0 Hz, 1H, Ar-H), 8.40 (d, J = 2.5 Hz, 1H, Ar-H), 8.00 (d, J = 9.0 Hz, 1H, Ar-H), 7.84 (dd, J = 9.0, 2.0 Hz, 1H, Ar-H), 7.52 (d, J = 5.0 Hz, 1H, Ar-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.5% | for 2 h; | Synthesis of Compound 3a (29.0 g, 0.130 mol)Add to a 500 mL three-necked flask,Heat and stir until dissolved.Further, a mixture of nitric acid (40.95 g, 0.650 mol) and propionic acid (10 mL) was slowly added dropwise to the reaction flask.After the addition is completed, the reaction is further carried out for 2 hours.TLC detection [V (dichloromethane): V (methanol) = 15:1] The reaction was completed, cooled, filtered,The filter residue is added to the ice saturated sodium bicarbonate solution and stirred.Filtered,The residue is dry,The compound was obtained as a yellow solid (26.0 g, yield: 64.5percent). |
50.2% | With nitric acid In propionic acid at 125℃; for 2 h; | The solution of compound 2g (20 mmol, 4.48 g) in propionic acid (30 mL) was heated to 125 ℃ and the mixture of nitric acid (0.89 mL) and propionic acid (6.27 mL) was added dropwise for 1 h. Then the mixture was reacted for 1 h and precipitated by petroleum ether. The solid was filtered and washed with diethyl ether. Yield 50.2percent. HPLC purity: 98.1percent. |
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