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[ CAS No. 65340-70-7 ] {[proInfo.proName]}

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Chemical Structure| 65340-70-7
Chemical Structure| 65340-70-7
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Product Details of [ 65340-70-7 ]

CAS No. :65340-70-7 MDL No. :MFCD00511001
Formula : C9H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :KJILYZMXTLCPDQ-UHFFFAOYSA-N
M.W : 242.50 Pubchem ID :5139537
Synonyms :

Calculated chemistry of [ 65340-70-7 ]

Physicochemical Properties

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 : 0.0
Molar Refractivity : 54.45
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 3.51
Log Po/w (WLOGP) : 3.65
Log Po/w (MLOGP) : 3.12
Log Po/w (SILICOS-IT) : 3.76
Consensus Log Po/w : 3.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.17
Solubility : 0.0163 mg/ml ; 0.0000674 mol/l
Class : Moderately soluble
Log S (Ali) : -3.46
Solubility : 0.0833 mg/ml ; 0.000343 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.17
Solubility : 0.00162 mg/ml ; 0.00000668 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.44

Safety of [ 65340-70-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P305+P351+P338-P302+P352-P304+P340-P312-P362+P364-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65340-70-7 ]

* 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 [ 65340-70-7 ]
  • Downstream synthetic route of [ 65340-70-7 ]

[ 65340-70-7 ] Synthesis Path-Upstream   1~18

  • 1
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YieldReaction ConditionsOperation 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).

Reference: [1] Patent: US2006/63805, 2006, A1, . Location in patent: Page/Page column 9
[2] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[3] Patent: US2015/320727, 2015, A1, . Location in patent: Paragraph 0557; 0558
[4] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[5] Patent: WO2006/132739, 2006, A2, . Location in patent: Page/Page column 48
[6] Patent: WO2014/22128, 2014, A1, . Location in patent: Paragraph 0144; 0145; 0155
[7] Patent: CN103539777, 2016, B, . Location in patent: Paragraph 0276; 0323; 0324
[8] Journal of the Chemical Society, 1950, p. 384,389
[9] Patent: WO2012/116237, 2012, A2, . Location in patent: Page/Page column 120
[10] Patent: WO2011/84402, 2011, A1, . Location in patent: Page/Page column 144-145
[11] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 96 - 105
[12] Journal of the Brazilian Chemical Society, 2014, vol. 25, # 5, p. 980 - 986
[13] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00641
[14] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 77; 78
[15] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 366
  • 2
  • [ 145369-94-4 ]
  • [ 65340-70-7 ]
YieldReaction ConditionsOperation 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).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[2] Patent: CN106432073, 2017, A, . Location in patent: Paragraph 0026; 0027; 0036; 0037; 0045; 0046; 0056; 0057
[3] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 41-42
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 3
  • [ 98948-95-9 ]
  • [ 65340-70-7 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Patent: WO2012/116237, 2012, A2,
[3] Patent: WO2014/151147, 2014, A1,
[4] Patent: US2015/30588, 2015, A1,
[5] Patent: US2015/320727, 2015, A1,
[6] Patent: US9295673, 2016, B2,
[7] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[8] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[9] Patent: CN106432073, 2017, A,
[10] Patent: WO2006/132739, 2006, A2,
  • 4
  • [ 122794-99-4 ]
  • [ 65340-70-7 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Patent: WO2012/116237, 2012, A2,
[3] Patent: WO2014/151147, 2014, A1,
[4] Patent: US2015/30588, 2015, A1,
[5] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[6] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[7] Patent: US2015/320727, 2015, A1,
[8] Patent: US9295673, 2016, B2,
[9] Patent: CN106432073, 2017, A,
[10] Patent: WO2006/132739, 2006, A2,
  • 5
  • [ 106-40-1 ]
  • [ 65340-70-7 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] Patent: WO2012/116237, 2012, A2,
[3] Patent: WO2014/22128, 2014, A1,
[4] Patent: WO2014/151147, 2014, A1,
[5] Patent: US2015/30588, 2015, A1,
[6] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[7] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[9] Patent: US2015/320727, 2015, A1,
[10] Patent: US9295673, 2016, B2,
[11] Patent: CN103539777, 2016, B,
[12] Patent: CN106432073, 2017, A,
[13] Patent: CN106432073, 2017, A,
[14] Patent: CN106432073, 2017, A,
[15] Patent: WO2006/132739, 2006, A2,
  • 6
  • [ 29124-64-9 ]
  • [ 68-12-2 ]
  • [ 65340-70-7 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 7, p. 541 - 544
  • 7
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Reference: [1] Journal of the Chemical Society, 1950, p. 384,389
[2] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[3] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[4] Patent: CN106432073, 2017, A,
  • 8
  • [ 187278-01-9 ]
  • [ 65340-70-7 ]
Reference: [1] Patent: WO2014/22128, 2014, A1,
[2] Patent: CN103539777, 2016, B,
[3] Patent: CN106432073, 2017, A,
  • 9
  • [ 19056-84-9 ]
  • [ 65340-70-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
  • 10
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Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
  • 11
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Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
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Reference: [1] Patent: CN106432073, 2017, A,
  • 13
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  • [ 65340-73-0 ]
YieldReaction ConditionsOperation in experiment
43% at 180℃; for 5 h; A reaction flask with a stir bar was charged with 6-bromo-4-chloroquinoline 17 (500mg, 2.1mmol), acetamide (2.438g, 41.3mmol), and K2CO3 (1.449g, 10.5mmol). The mixture was heated to 180 °C for 5 h and was allowed to cool to ambient temperature followed by adding water (50ml). The solution was extracted with ethyl acetate (20ml × 3), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography (DCM:MeOH=20:1) to provide 6-bromoquinolin-4-amine 18 (198mg, yield = 43percent).1H NMR (400 MHz, DMSO-d6) δ 8.46 (d, J = 2.2 Hz, 1H), 8.25 (d, J = 7.2 Hz, 1H), 7.95 (dd, J = 8.9, 2.3 Hz, 1H), 7.69 (d, J = 8.9 Hz, 1H), 7.12 (d, J = 7.2 Hz, 1H), 5.64 (s, 2H). LC-MS (ESI) m/z = 223.1, 225.1 (M+H, M+2+H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1919 - 1922
  • 14
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  • [ 874792-20-8 ]
YieldReaction ConditionsOperation in experiment
90.8% at 20 - 120℃; for 15 h; To a solution of 6-bromo-4-chloro-quinoline (12.12 g, 50 mmol) in methanol (200 mL) was added sodium methoxide (13.50 g, 250 mmol) at room temperature.
Then, the reaction mixture was heated to 120° C. for 15 h in a sealed reaction flask.
After cooling to room temperature, the methanol was removed under the vacuum and the residue was diluted with water.
Then, the solids were collected by filtration and washed with water.
After drying in air, 10.8 g (90.8percent yield) of 6-bromo-4-methoxy-quinoline was isolated as a white solid which can be crystallized from acetonitrile: EI-HRMS m/e calcd for C10H8BrNO (M+) 236.9789, found 236.9784.
36% at 120℃; for 1 h; Microwave irradiation 300 mg (1.24 mmol) of 6-bromo-4-chloroquinoline [Lin et al., J. Med. Chem. 1978, 21, 268] was taken up in 4 ml methanol and 1.15 ml (6.19 mmol) methanolic sodium methylate solution (30 wt.percent) was added. Then it was reacted in a single mode microwave for 1 h at 1200C. The solvent was removed in a rotary evaporator and the residue was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried over magnesium sulfate. The solvent was removed by distillation at reduced pressure. In this way we obtained 150 mg (36percent of theor.) of the target compound.LC-MS (method 2): R, = 1.24 min; MS (EIpos): m/z = 238 [M]+.
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 8, p. 730 - 734
[2] Patent: US2006/63805, 2006, A1, . Location in patent: Page/Page column 9
[3] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 115
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Reference: [1] Patent: WO2011/84402, 2011, A1, . Location in patent: Page/Page column 145
  • 16
  • [ 65340-70-7 ]
  • [ 74-89-5 ]
  • [ 916812-31-2 ]
YieldReaction ConditionsOperation in experiment
41% at 120℃; for 3 h; Microwave irradiation 6-Bromo-N-methyl-4-quinolinamine. The mixture of the compound fromExample 22 a) (100 mg, 0.41 mmol) and methylamine (2.0 M in methanol, 2 mL, 4 mmol) was heated to 120 0C for 3 hours in a Biotage Initiator microwave synthesizer. The product was cooled, concentrated and purified via flash chromatography (0-10percent methanol in methylene chloride) to afford the title compound as a white solid (40 mg, 41 percent). 1 H NMR (400 MHz, CHLOROFORM-o) δ ppm 8.39 (d, J=5.81 Hz, 1 H) 8.04 (d, J=1.77 Hz, 1 H) 7.80 (d, J=9.09 Hz, 1 H) 7.67 (dd, J=8.84, 2.02 Hz, 1 H) 6.37 (d, J=5.81 Hz, 1 H) 3.02(s, 3 H).
Reference: [1] Patent: WO2006/132739, 2006, A2, . Location in patent: Page/Page column 46
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  • [ 927801-23-8 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 1, p. 39 - 43
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
[3] Patent: WO2014/22128, 2014, A1,
[4] Patent: CN103539777, 2016, B,
  • 18
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  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
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