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Chemical Structure| 17285-36-8 Chemical Structure| 17285-36-8

Structure of 17285-36-8

Chemical Structure| 17285-36-8

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Product Details of [ 17285-36-8 ]

CAS No. :17285-36-8
Formula : C4H2Cl2N2O
M.W : 164.98
SMILES Code : ClC1=CC(=O)NN=C1Cl
MDL No. :MFCD04971420
InChI Key :RWDZPWHMUXKPMN-UHFFFAOYSA-N
Pubchem ID :320690

Safety of [ 17285-36-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 17285-36-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 34.88
TPSA ?

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

45.75 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.24
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

1.17
Log Po/w (WLOGP)?

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

1.08
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.

1.05
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

2.5
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.41

Water Solubility

Log S (ESOL):?

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

-2.09
Solubility 1.33 mg/ml ; 0.00807 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.

-1.73
Solubility 3.1 mg/ml ; 0.0188 mol/l
Class?

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

Very 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

-2.78
Solubility 0.272 mg/ml ; 0.00165 mol/l
Class?

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

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

No
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.

-6.48 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

2.0
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

0.0 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<1.0
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)

1.84

Application In Synthesis of [ 17285-36-8 ]

* 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.

  • Downstream synthetic route of [ 17285-36-8 ]

[ 17285-36-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 6082-66-2 ]
  • [ 64-19-7 ]
  • [ 17285-37-9 ]
  • [ 17285-36-8 ]
  • 2
  • [ 6082-66-2 ]
  • [ 17285-37-9 ]
  • [ 17285-36-8 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; at 100.0℃; for 12.0h; A solution of 3,4,6-trichloropyridazine (20.0 g, 109.04 mmol) in HOAc (100 mL) was heated at 100 °C for 12 h, at which time TLC indicated the reaction had gone to completion. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (petroleum ether : Ethyl acetate = 1 : 1 ) to give the title compounds (11.2 g, 63percent yield) (1 : 1 ratio of regioisomers) as a white solid. LCMS M/Z (M+H) 165.
  • 3
  • [ 6082-66-2 ]
  • [ 17285-36-8 ]
YieldReaction ConditionsOperation in experiment
3.7 g With acetic acid; at 130.0℃; for 2.0h; 3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130 °C for two hours. After cooling to room temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound.
3.7 g With acetic acid; at 130.0℃; for 2.0h; Example 18A 5,6-dichloropyridazin-3(2H)-one [0749] 3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130° C. for two hours. After cooling to room temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound.
3.7 g With acetic acid; at 130.0℃; for 2.0h; 3,4,6-Trichloropyridazine (12 g, 65.4 mmol) in acetic acid (45 mL) was heated at 130 °C for two hours. After cooling to ambient temperature, the reaction mixture was poured into ice water (200 mL). The solid was collected by filtration to give 3.7 g of the title compound.
  • 4
  • [ 17285-36-8 ]
  • [ 17285-22-2 ]
  • 5
  • [ 186581-53-3 ]
  • [ 17285-36-8 ]
  • [ 112342-59-3 ]
  • [ 6794-35-0 ]
  • 6
  • [ 17285-36-8 ]
  • [ 999-97-3 ]
  • [ 87009-00-5 ]
  • 7
  • [ 17285-36-8 ]
  • [ 10416-58-7 ]
  • [ 87009-00-5 ]
  • 9
  • [ 17285-36-8 ]
  • [ 100-39-0 ]
  • [ 1051923-57-9 ]
  • 10
  • [ 17285-36-8 ]
  • [ 10365-98-7 ]
  • 5-chloro-6-(3-methoxyphenyl)pyridazin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
360 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; at 85.0℃; for 16.0h;Inert atmosphere; A. 5-Chloro-6-(3-methoxyphenyl)pyridazin-3(2H)-one. To a 50-mL round-bottom flask was placed a solution of <strong>[17285-36-8]5,6-dichloro-2,3-dihydropyridazin-3-one</strong> (990 mg, 6.00 mmol) and (3- methoxyphenyl)boronic acid (900 mg, 5.91 mmol) in EtOH (45 mL) and water (9 mL) then Na2C03 (1062 mg, 10.02 mmol) and Pd(PPh3)4 (288 mg, 0.24 mmol) were added under nitrogen. The reaction was stirred for 16 h at 85°C, cooled to rt, and concentrated under reduced pressure. The residue was purified by column chromatography eluting with EtO Ac/petroleum ether (2: 1) affording 360 mg of the title compound as a white solid. Mass Spectrum (LCMS, ESI pos): Calcd. for CiiH10ClN2O2+: 237.0 (M+H); Found: 237.0.
 

Historical Records

Technical Information

Categories

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[ 17285-36-8 ]

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Related Parent Nucleus of
[ 17285-36-8 ]

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