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Chemical Structure| 13108-52-6 Chemical Structure| 13108-52-6

Structure of 13108-52-6

Chemical Structure| 13108-52-6

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Product Details of [ 13108-52-6 ]

CAS No. :13108-52-6
Formula : C6H3Cl4NO2S
M.W : 294.97
SMILES Code : O=S(C1=C(Cl)C(Cl)=NC(Cl)=C1Cl)(C)=O
MDL No. :MFCD00054553
InChI Key :NMCCNOZOBBWFMN-UHFFFAOYSA-N
Pubchem ID :61579

Safety of [ 13108-52-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 13108-52-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 57.37
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

55.41 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.45
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.14
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.18
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.27
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.35
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.68

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.27
Solubility 0.159 mg/ml ; 0.000539 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.94
Solubility 0.342 mg/ml ; 0.00116 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.79
Solubility 0.00475 mg/ml ; 0.0000161 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.58 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<0.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.31

Application In Synthesis of [ 13108-52-6 ]

* 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 [ 13108-52-6 ]

[ 13108-52-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 22963-62-8 ]
  • [ 13108-52-6 ]
YieldReaction ConditionsOperation in experiment
96% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Cooling with ice 2,3,5,6-tetrachloro-4-mercaptopyridine (10 g, 38.0 mmol)Dissolved in dichloromethane DCM) (80 mL)Ice water bath cooling,Were added over 15 minutes in three portions each batch compartmentM-chloroperoxybenzoic acid (14.4 g, 83.6 mmol).The reaction solution was allowed to react at room temperature for three hours.GC detection of raw materials have been completed.The reaction solution was washed with (2 x 20 mL) saturated sodium carbonate solution,And then washed with (2 x 20 mL)The organic phase was dried over anhydrous sodium sulfate,Filtered and concentrated under reduced pressure crude,The crude product was added with ethanol (5 mL)Filtered and dried to give (10.8 g, 96percent)2,3,5,6-tetrachloro-4-methanesulfonylpyridine.
92.3% With sodium tungstate; dihydrogen peroxide; acetic acid In water at 30 - 85℃; Large scale Add 90kg of tetrahydrofuran and 30kg of pentachloropyridine to the 200L enamel reactor, turn on the stirring and control the temperature to 20±5°C to slowly add 41.7kg of sodium methylthioate aqueous solution with the concentration of 20percent. After the completion of the addition, the reaction is kept for 1h. The HPLC controlled reaction was complete. After phase separation, the organic phase is subjected to atmospheric distillation to recover tetrahydrofuran.Then adding 90 kg of glacial acetic acid to the organic phase,Catalyst sodium tungstate 0.3kg,When the temperature is controlled at 30 to 40 ° C, 5.7 kg of hydrogen peroxide is added dropwise.Warm up to 60-75 ° C and continue to add 5.7 kg of hydrogen peroxide.Finally, when the temperature is controlled at 75-85 ° C, 5.7 kg of hydrogen peroxide is added dropwise.After the completion of the HPLC reaction,The crystals were cooled to 20 to 25 ° C, centrifuged, rinsed and dried to obtain 32.47 kg of 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, the content was 99.8percent, and the yield was 92.3percent.
References: [1] Patent: CN106478494, 2017, A, . Location in patent: Paragraph 0019; 0022; 0025; 0028; 0031; 0035; 0040; 0041.
[2] Patent: CN108794389, 2018, A, . Location in patent: Paragraph 0037; 0038-0044; 0051-0055.
 

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