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[ CAS No. 13676-02-3 ] {[proInfo.proName]}

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Chemical Structure| 13676-02-3
Chemical Structure| 13676-02-3
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Product Details of [ 13676-02-3 ]

CAS No. :13676-02-3 MDL No. :MFCD00799212
Formula : C10H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :ZFEJTYQUWRVCFW-UHFFFAOYSA-N
M.W : 193.63 Pubchem ID :83647
Synonyms :

Calculated chemistry of [ 13676-02-3 ]

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) : -5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 2.68
Log Po/w (WLOGP) : 2.9
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 3.06
Consensus Log Po/w : 2.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.113 mg/ml ; 0.000586 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.309 mg/ml ; 0.0016 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 : 1.46

Safety of [ 13676-02-3 ]

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 [ 13676-02-3 ]

* 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 [ 13676-02-3 ]
  • Downstream synthetic route of [ 13676-02-3 ]

[ 13676-02-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 13676-02-3 ]
  • [ 577967-89-6 ]
YieldReaction ConditionsOperation in experiment
93% With boron tribromide In dichloromethane at 0 - 20℃; for 15 h; General procedure: To a cooled solution of aryl methyl ether ( 1.0 equiv.) in DCM (10 mL) was added BBr3 (5.0 equiv.) slowly. The resulting mixture was stirred at 0 C and then warmed gradually to room temperature, and. stirred at room temperature for 15 hrs. After the reaction was completed, the reaction was quenched with NaHCO3 solution (50 mL) and extracted with DCM (4 × 10 mL). The combined organic layers were washed with H2O (3 × 10 mL), dried (Na2SO4) and concentrated in vacuo to afford the expected phenols. 2-chloroquinolin-6-ol: DHK-6-71 was prepared using general procedure G. Reaction was performed on a 2 g scale. DHK-6-71 was isolated as yellow solid. (1.72 g. 93percent).
70%
Stage #1: With boron tribromide In dichloromethane at 0 - 25℃; for 2 h;
Stage #2: With ammonium chloride In dichloromethane; water
To a solution of 2-chloro-6-methoxyquinoline (Intermediate 1) (2.00 g, 10.4 mmol) in anhydrous DCM (100 mL) was added BBr3 (6 mL, 62.2 mmol) dropwise at 0°C. The reaction mixture was stirred at 25°C for 2 hours, then quenched with aqueous saturated NH4C1 (50 mL) and filtered. The filtrate was extracted with CH2C12 / MeOH (v / v =10 / 1, 30 mL x2) and the combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give 2-chloroquinolin-6-ol (1.30 g, yield 70percent) as yellow solid. 1H NMR (CDC13 300 MHz): δ 7.95 (t, J = 8.1 Hz, 2H), 7.35 (dd, J = 6.0, 3.3 Hz, 2H), 7.13 (d, J = 2.7 Hz, 1H).
70%
Stage #1: With boron tribromide In dichloromethane at 0 - 25℃; for 2 h;
Stage #2: With ammonium chloride In dichloromethane; water at 25℃;
To a solution of 2-chloro-6-methoxyquinoline (Intermediate 1) (2.00 g, 10.4 mmol) in anhydrous DCM (100 mL) was added BBr3 (6 mL, 62.2 mmol) dropwise at 0°C. The reaction mixture was stirred at 25 °C for 2 hours, then quenched with aqueous saturated NH4C1 (50 mL) and filtered. The filtrate was extracted with CH2C12 / MeOH (v / v =10 / 1, 30 mL x2) and the combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give 2-chloroquinolin-6-ol (1.30 g, yield 70percent) as yellow solid. *H NMR (CDC13 300 MHz): δ 7.95 (t, / = 8.1 Hz, 2H), 7.35 (dd, / = 6.0, 3.3 Hz, 2H), 7.13 (d, / = 2.7 Hz, 1H).
Reference: [1] Patent: CN102985411, 2016, B, . Location in patent: Paragraph 0906-0908
[2] Patent: WO2012/48181, 2012, A1, . Location in patent: Page/Page column 74
[3] Patent: WO2012/83165, 2012, A1, . Location in patent: Page/Page column 91
[4] ACS Chemical Neuroscience, 2016, vol. 7, # 7, p. 897 - 911
[5] Journal of the American Chemical Society, 1951, vol. 73, p. 4837
  • 2
  • [ 5392-11-0 ]
  • [ 13676-02-3 ]
YieldReaction ConditionsOperation in experiment
57% With trichloroisocyanuric acid; triphenylphosphine In neat (no solvent) at 160 - 170℃; for 15 h; Inert atmosphere General procedure: Ina flask (50 mL) equipped with a magnetic stirrer bar and balloon, a mixture of triphenylphosphine (1191mg, 4.54 mmol) and trichloroisocyanuric acid (360 mg, 1.55 mmol) was heated under an argonatmosphere. During the heating process, triphenylphosphine melted, and trichloroisocyanuric acidvigorously reacted at 130-140 °C to form a dark brown oil, followed by further heating for 10 min.1-Methylquinolin-2(1H)-one (242 mg, 1.50 mmol) was added to the mixture followed by heating at130-140 °C for 3 h. Then, the reaction mixture was dissolved in CH2Cl2 and basified with triethylaminefollowed by silica gel column chromatography using hexane-EtOAc (6:1) as an eluate. The product2-chloroquinoline (204 mg, 82percent) was obtained.
Reference: [1] Heterocycles, 2015, vol. 91, # 7, p. 1445 - 1454
[2] Pr. roy. Soc. <B>, 1931, vol. 108, p. 130,131
  • 3
  • [ 13676-00-1 ]
  • [ 13676-02-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 22, p. 5405 - 5417
[2] Patent: WO2004/24731, 2004, A1, . Location in patent: Page 56
[3] Patent: US2007/173508, 2007, A1, . Location in patent: Page/Page column 84
[4] Patent: US2002/82276, 2002, A1,
  • 4
  • [ 13676-00-1 ]
  • [ 13676-02-3 ]
YieldReaction ConditionsOperation in experiment
86% for 2 h; Reflux A solution of 6- methoxyquinolin-2-ol (400 mg, 2.29 mmol) in POCI3 (5.0 mL) was refluxed for 2 hours. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc (50 mL), the organic layer was washed with saturated NaHC03 (30 mL x2), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by silica gel column (PE / EtOAc=10 / 1) to give 2-chloro-6-methoxyquinoline (380 mg, yield 86percent) as a solid. 1H NMR (CDC13 400 MHz): δ 7.92 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 9.2 Hz, 1H), 7.32-7.25 (m, 2H), 7.00 (d, J = 2.4 Hz, 1H), 3.86 (s, 3H).
86% for 2 h; Reflux A solution of 6- methoxyquinolin-2-ol (400 mg, 2.29 mmol) in POCI3 (5.0 mL) was refluxed for 2 hours. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc (50 mL), the organic layer was washed with saturated NaHCC>3 (30 mL x2), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by silica gel column (PE / EtOAc=10 / 1) to give 2-chloro-6-methoxyquinoline (380 mg, yield 86percent) as a solid. *H NMR (CDC13 400 MHz): δ 7.92 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 9.2 Hz, 1H), 7.32-7.25 (m, 2H), 7.00 (d, / = 2.4 Hz, 1H), 3.86 (s, 3H).
Reference: [1] Patent: WO2012/48181, 2012, A1, . Location in patent: Page/Page column 74
[2] Patent: WO2012/83165, 2012, A1, . Location in patent: Page/Page column 91
[3] Ann. Inst. Pasteur, 1930, vol. 44, p. 719,736
  • 5
  • [ 6563-13-9 ]
  • [ 13676-02-3 ]
  • [ 4295-04-9 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 792 - 795
[2] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7130 - 7132
  • 6
  • [ 6563-13-9 ]
  • [ 13676-02-3 ]
YieldReaction ConditionsOperation in experiment
46% With trichlorophosphate In chloroform Step 1a
A solution of 6-methoxyquinoline N-oxide (5.0 g, 29 mmol) in CHCl3 (30 mL) was treated by slow addition of POCl3 (5.3 mL, 57 mmol) at 0° C.
The mixture was heated at 80° C. for 14 hours.
The mixture was cooled and poured onto ice.
After stirring for 30 min., the aqueous layer was adjusted to pH 9 by Na2CO3 addition.
The mixture was extracted with CH2Cl2.
The organic layer was worked-up. HPLC (1:10 EtOAc/hexane) gave 2.5 g (46percent) of 2-chloro-6-methoxyquinoline as a white solid, (M+) 193(100).
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[2] Patent: WO2012/48181, 2012, A1,
[3] Patent: WO2012/83165, 2012, A1,
[4] Patent: US2002/82276, 2002, A1,
  • 7
  • [ 5263-87-6 ]
  • [ 13676-02-3 ]
Reference: [1] Patent: WO2012/48181, 2012, A1,
[2] Patent: WO2012/83165, 2012, A1,
[3] Heterocycles, 2015, vol. 91, # 7, p. 1445 - 1454
[4] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
  • 8
  • [ 340258-61-9 ]
  • [ 13676-02-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 22, p. 5405 - 5417
  • 9
  • [ 19315-93-6 ]
  • [ 13676-02-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1678 - 1681
  • 10
  • [ 577967-89-6 ]
  • [ 74-88-4 ]
  • [ 13676-02-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1678 - 1681
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