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[ CAS No. 160893-07-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 160893-07-2
Chemical Structure| 160893-07-2
Chemical Structure| 160893-07-2
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Product Details of [ 160893-07-2 ]

CAS No. :160893-07-2 MDL No. :MFCD22394142
Formula : C10H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :ACMDJXKHEUGSIS-UHFFFAOYSA-N
M.W : 193.63 Pubchem ID :11019719
Synonyms :

Calculated chemistry of [ 160893-07-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.25
TPSA : 22.12 Ų

Pharmacokinetics

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) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 3.12
Log Po/w (WLOGP) : 2.9
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.51
Solubility : 0.0599 mg/ml ; 0.00031 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.108 mg/ml ; 0.000558 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.45
Solubility : 0.00692 mg/ml ; 0.0000357 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 160893-07-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 160893-07-2 ]

* 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 [ 160893-07-2 ]
  • Downstream synthetic route of [ 160893-07-2 ]

[ 160893-07-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 6931-19-7 ]
  • [ 160893-07-2 ]
YieldReaction ConditionsOperation in experiment
32%
Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3.5 h;
Stage #2: With trichlorophosphate In dichloromethane at 60℃; for 3 h;
Example 1 2-Chloro-5-methoxyquinoline [0085] After 5-methoxyquinoline (104.3 mg, 0.655 mmol) was dissolved in dichloromethane (3 mL), meta-chloroperbenzoic acid (mCPBA; 195 mg, 1.13 mmol) was added thereto at 0° C., and the resulting mixture was stirred for 30 min. After the stirring for 30 min, the reaction temperature was increased from 0° C. to room temperature, followed by further stirring for 3 hr. The completion of the reaction was confirmed by TLC (EtOAc/MC/Hexane=1:2:4). When the reaction was completed, the reaction mixture was extracted with an aqueous solution of 4 N NaOH and dichloromethane, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The resulting filtrate was concentrated under reduced pressure, to thereby generate a white solid. The thus generated solid was dissolved in dichloromethane (2.5 mL) and added with phosphorous oxychloride (POCl3; 0.09 mL, 0.992 mmol). The resulting mixture was subjected to distillation under reflux at 60° C. for 3 hr. The completion of the reaction was confirmed by TLC (EtOAc/CHCl3/Hexane=1:2:10). When the reaction was completed, the reactant was cooled down to room temperature, followed by further cooling down with the gentle addition of ice. The pH of the resulting mixture was then adjusted to 10 by dropwise addition of an aqueous solution of 4 N NaOH. When the pH was adjusted to 10, the reaction mixture was extracted with distilled water and dichloromethane, to thereby separate an organic layer. The organic layer was dried over anhydrous MgSO4 and filtered. The resulting filtrate was concentrated under reduced pressure and purified by column chromatography (EtOAc/CHCl3/Hexane=1:2:10, R.f: 0.6), to thereby obtain 2-chloro-5-methoxyquinoline (40.1 mg, 32percent) as a white solid. [0086] 1H NMR (CDCl3, 300 MHz) δ 4.01 (s, 3H), 6.88 (dd, J=7.2, 1.5 Hz, 1H), 7.35 (d, J=8.7 Hz, 1H), 7.59-7.67 (m, 2H), 8.51 (d, J=8.7 Hz, 1H)
Reference: [1] Patent: US2014/206876, 2014, A1, . Location in patent: Paragraph 0085-0086
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[3] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2304 - 2310
[4] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 754 - 768
[5] Patent: KR101778938, 2017, B1,
  • 2
  • [ 90924-16-6 ]
  • [ 160893-07-2 ]
YieldReaction ConditionsOperation in experiment
40.1 mg With trichlorophosphate In dichloromethane at 60℃; for 3 h; Inert atmosphere To solution of 5-methoxyquinoline 2a (104 mg, 0.66 mmol) in CH2Cl2 (3 mL) was added meta-chloroperoxybenzoic acid (195 mg, 1.13 mmol) at 0 °C for 30 min. The mixture was allowed to warm to room temperature and stirred for additional 3 h. The reaction is queched with 4 N NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give the crude N-oxide, which was directly used for the next step without purification. To solution of the resulting N-oxide in CH2Cl2 (2.5 mL) was adeed phosphorus oxychloride (0.09 mL, 0.99 mmol). The reaction mixture was refluxed at 60 °C for 3 h, allowed to cool to room temperature and poured into ice-water. The resulting mixture was treated with 4 N aqueous NaOH until pH reached to around 10. The organic phase was extracted with CH2Cl2 (3 x 5 mL), washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOA/CH2Cl2/Hexane = 1:2:4) to give 5-methoxy-2chloroquinoline 4a (40.1 mg, 32percent)
40.1 mg With trichlorophosphate In dichloromethane at 60℃; for 3 h; Inert atmosphere General procedure: To solution of 5-methoxyquinoline 6a (104 mg, 0.66 mmol) in CH2Cl2 (3mL) was added meta-chloroperoxybenzoic acid (195 mg, 1.13 mmol) at 0 °C for 30 min. The mixture was allowed to warm to room temperature and stirred for additional 3 h. The reaction is queched with 4 N NaOH and extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give the crude N-oxide, which was directly used for the next step without purification. To solution of the resulting N-oxide in CH2Cl2 (2.5 mL) was adeed phosphorus oxychloride (0.09 mL, 0.99 mmol). The reaction mixture was refluxed at 60 °C for 3 h, allowed to cool to room temperature and poured into ice-water. The resulting mixture was treated with 4 N aqueous NaOH until pH reached to around 10. The organic phase was extracted with CH2Cl2 (3 × 5 mL), washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/CH2Cl2/Hexane = 1:2:4) to give 2-chloro-5-methoxy-chloroquinoline 7a (40.1 mg, 32percent) as a white solid:1HNMR (CDCl3, 300 MHz) δ 4.01 (s, 3H), 6.88 (dd, J = 7.2,1.5 Hz, 1H), 7.35 (d, J = 8.7 Hz, 1H), 7.59-7.67 (m, 2H),8.51 (d, J = 8.7 Hz, 1H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3307 - 3312
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[3] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2304 - 2310
[4] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 754 - 768
[5] Chemical Biology and Drug Design, 2017, vol. 89, # 1, p. 98 - 113
[6] Patent: KR101778938, 2017, B1,
  • 3
  • [ 160893-04-9 ]
  • [ 160893-07-2 ]
YieldReaction ConditionsOperation in experiment
86% for 1 h; Reflux 4.5
2-Chloro-5-methoxyquinoline (4)
Phosphorus oxychloride (25.0 mL, 268.0 mmol) was added to compound 3 (2.65 g, 15.15 mmol) at rt and the resulting suspension was heated under reflux for 1 h.
The reaction mixture was allowed to cool to rt, poured onto ice cold water (300 mL) and cautiously neutralized with diluted aqueous ammonium hydroxide in ice bath.
The mixture was extracted with DCM (3 * 150 mL) and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure to afford the title compound; yellow solid; yield: 2.5 g (86percent); 1H NMR (400 MHz, CDCl3) δ 8.46 (d, J = 8.8 Hz, 1H), 7.59 (dd, J = 10.0, 8.0 Hz, 2H), 7.31 (d, J = 8.4 Hz, 1H), 6.84 (t, J = 7.2 Hz, 1H), 3.97 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 155.17, 151.03, 148.61, 133.97, 130.80, 121.07, 120.37, 119.20, 104.81, 55.77.
86% for 1 h; Inert atmosphere; Reflux (5) under an argon atmosphere, manufactured by 5-methoxyquinolin-2(1H)-one (2.7 g, 15.2 mmol) was added phosphorus oxychloride (25.0 mL, 268.0 mmol) and the mixture was refluxed for 1 hour, The completion of the reaction was confirmed by TLC (hexane: ethyl acetate = 1: 1). The reaction mixture was poured into ice water (300 mL), After neutralization with ammonia water (65 mL) and extracted with dichloromethane (3 X 150 mL). The organic solvent layer was washed again with a saturated sodium chloride solution (450 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent to obtain the title compound (2.5 g, 86percent yield).
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 754 - 768
[2] Patent: KR101778938, 2017, B1, . Location in patent: Paragraph 0147-0148; 0155; 0180-0182
  • 4
  • [ 578-67-6 ]
  • [ 160893-07-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1472 - 1476
[2] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 8, p. 2304 - 2310
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 754 - 768
[4] Chemical Biology and Drug Design, 2017, vol. 89, # 1, p. 98 - 113
[5] Patent: KR101778938, 2017, B1,
  • 5
  • [ 186581-53-3 ]
  • [ 124467-35-2 ]
  • [ 160893-07-2 ]
Reference: [1] Heterocycles, 1994, vol. 38, # 12, p. 2615 - 2620
  • 6
  • [ 607-34-1 ]
  • [ 160893-07-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3307 - 3312
[2] Chemical Biology and Drug Design, 2017, vol. 89, # 1, p. 98 - 113
[3] Patent: KR101778938, 2017, B1,
  • 7
  • [ 611-34-7 ]
  • [ 160893-07-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3307 - 3312
[2] Patent: KR101778938, 2017, B1,
  • 8
  • [ 160893-07-2 ]
  • [ 160893-04-9 ]
Reference: [1] Heterocycles, 1994, vol. 38, # 12, p. 2615 - 2620
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