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[ CAS No. 874792-20-8 ] {[proInfo.proName]}

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Chemical Structure| 874792-20-8
Chemical Structure| 874792-20-8
Structure of 874792-20-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 874792-20-8 ]

CAS No. :874792-20-8 MDL No. :MFCD04036192
Formula : C10H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :AWLGLUBASOBKNM-UHFFFAOYSA-N
M.W :238.08 Pubchem ID :45790929
Synonyms :

Calculated chemistry of [ 874792-20-8 ]

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 : 55.94
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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 2.85
Log Po/w (WLOGP) : 3.01
Log Po/w (MLOGP) : 2.19
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 2.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.61
Solubility : 0.0578 mg/ml ; 0.000243 mol/l
Class : Soluble
Log S (Ali) : -2.97
Solubility : 0.253 mg/ml ; 0.00106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.69
Solubility : 0.00489 mg/ml ; 0.0000206 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 874792-20-8 ]

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 [ 874792-20-8 ]

* 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 [ 874792-20-8 ]
  • Downstream synthetic route of [ 874792-20-8 ]

[ 874792-20-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 65340-70-7 ]
  • [ 124-41-4 ]
  • [ 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
  • 2
  • [ 927801-23-8 ]
  • [ 124-41-4 ]
  • [ 874792-20-8 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 4, p. 2342 - 2350
  • 3
  • [ 67-56-1 ]
  • [ 65340-70-7 ]
  • [ 124-41-4 ]
  • [ 874792-20-8 ]
Reference: [1] Patent: WO2011/84402, 2011, A1, . Location in patent: Page/Page column 145
  • 4
  • [ 145369-94-4 ]
  • [ 874792-20-8 ]
Reference: [1] Patent: WO2011/84402, 2011, A1,
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