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[ CAS No. 6456-78-6 ] {[proInfo.proName]}

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Chemical Structure| 6456-78-6
Chemical Structure| 6456-78-6
Structure of 6456-78-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6456-78-6 ]

CAS No. :6456-78-6 MDL No. :MFCD02752433
Formula : C10H6ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GGHKFVNCVUIGRP-UHFFFAOYSA-N
M.W : 207.61 Pubchem ID :165492
Synonyms :

Calculated chemistry of [ 6456-78-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.71
TPSA : 50.19 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) : -5.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 2.34
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 1.9
Log Po/w (SILICOS-IT) : 2.43
Consensus Log Po/w : 2.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.179 mg/ml ; 0.000863 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.192 mg/ml ; 0.000926 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.7
Solubility : 0.0418 mg/ml ; 0.000201 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 6456-78-6 ]

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:

Application In Synthesis of [ 6456-78-6 ]

* 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 [ 6456-78-6 ]
  • Downstream synthetic route of [ 6456-78-6 ]

[ 6456-78-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 56-81-5 ]
  • [ 635-21-2 ]
  • [ 6456-78-6 ]
YieldReaction ConditionsOperation in experiment
68.91%
Stage #1: at 65 - 140℃; for 5.5 - 7.5 h;
Stage #2: at 0℃;
Example-2; 6-Chloro-l ,2,3,4-tetrahydro-quinoline-8-carboxylic acid (4-/er/-butyl-benzyl)-[2-(4- fluoro-phenyl)-ethyl]-amide, hydrochloride salt a) Concentrated sulfuric acid (73.83 g, 0.80 mol) was added dropwise to a vigorously stirred mixture of 2-amino-5-chloro-benzoic acid (90 g, 0.524 mol), I2 (1.65g, 6.4 mmol) in glycerol within 30 minutes, wherein the temperature of the mixture rises to 65-70 0C. The mixture was then heated to 135-140 0C for 5-7 hrs giving a dark brown foaming mixture. The reaction mixture was cooled to room temperature and poured into 1500 ml of ice water. The pH of the mixture was adjusted to 6.5 by adding 25-30 percent ammonia solution. The precipitated compound was filtered, washed with cold water and dried over P2O5 to get brown solid. of 6-chloro- quinoline-8-carboxylic acid (75 g) (Yield=68.91 percent).
68.91%
Stage #1: at 20 - 140℃;
Stage #2: With ammonia In water; glycerol
Concentrated sulfuric acid (73.83 g, 0.80 mol) was added dropwise to a vigorously stirred mixture of 2-amino-5-chloro-benzoic acid (90 g, 0.524 mol), I2 (1.65 g, 6.4 mmol) in glycerol within 30 minutes, wherein the temperature of the mixture rises to 65-70° C. The mixture was then heated to 135-140° C. for 5-7 hrs giving a dark brown foaming mixture. The reaction mixture was cooled to room temperature and poured into 1500 ml of ice water. The pH of the mixture was adjusted to 6.5 by adding 25-30percent ammonia solution. The precipitated compound was filtered, washed with cold water and dried over P2O5 to get brown solid of 6-chloro-quinoline-8-carboxylic acid (75 g) (Yield=68.91percent).
7.9% at 65 - 140℃; for 6.5 h; 1.01 g of 5-chloroanthranilic acid and 26.6 mg of iodine were mixed with 0.7 6 g of glycerol, and the mixture was vigorously stirred,0.44 ml of concentrated sulfuric acid was added dropwise at 65 ° C. to 70 ° C. over a period of 30 minutes and the reaction was carried out at 140 ° C. for 6 hours. Then,17 mL of water at 0 ° C. was added and the pH6.5 was filtered, the solid was washed with cold water and then dried. The obtained residue was dissolved in chloroform,Insolubles were removed by filtration, activated carbon was added to adsorb impurities, and the activated carbon was removed by filtration.The solvent was distilled off, and the residue obtained was recrystallized in a mixed solution of chloroform and ethyl acetate, and the obtained crystals were washed with ethyl acetate.The solvent was distilled off to obtain 96.2 mg (yield 7.9percent) of the compoundWas obtained. For this compound, NMR, mass spectrum,The melting point was measured, and the compound 2 having the structure of the general formula 3(6-chloroquinoline-8-carboxylic acid) was confirmed.
Reference: [1] Patent: WO2008/59513, 2008, A2, . Location in patent: Page/Page column 14
[2] Patent: US2009/171091, 2009, A1, . Location in patent: Page/Page column 6
[3] Patent: JP2018/52866, 2018, A, . Location in patent: Paragraph 0046
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