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Chemical Structure| 64690-19-3 Chemical Structure| 64690-19-3

Structure of 64690-19-3

Chemical Structure| 64690-19-3

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Product Details of [ 64690-19-3 ]

CAS No. :64690-19-3
Formula : C13H22N2
M.W : 206.33
SMILES Code : C1=C(NCCCCCCCC)C=CN=C1
MDL No. :MFCD09743883
InChI Key :RHDWCSIBVZKRRU-UHFFFAOYSA-N
Pubchem ID :3017535

Safety of [ 64690-19-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 64690-19-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.62
Num. rotatable bonds 8
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 67.19
TPSA ?

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

24.92 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.94
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

4.25
Log Po/w (WLOGP)?

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

3.66
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.

2.28
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

3.47
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.32

Water Solubility

Log S (ESOL):?

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

-3.56
Solubility 0.0562 mg/ml ; 0.000272 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.

-4.48
Solubility 0.00676 mg/ml ; 0.0000328 mol/l
Class?

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

Moderately 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

-5.3
Solubility 0.00103 mg/ml ; 0.00000498 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

Yes
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

Yes
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.

-4.54 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

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<3.0
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)

1.67

Application In Synthesis of [ 64690-19-3 ]

* 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 [ 64690-19-3 ]

[ 64690-19-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 504-24-5 ]
  • [ 124-13-0 ]
  • [ 64690-19-3 ]
References: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 11, p. 1457 - 1464.
[2] Patent: US4206215, 1980, A, .
  • 2
  • [ 111-86-4 ]
  • [ 19524-06-2 ]
  • [ 64690-19-3 ]
References: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596.
[2] Organic Letters, 2008, vol. 10, # 18, p. 4109 - 4112.
  • 3
  • [ 111-86-4 ]
  • [ 7379-35-3 ]
  • [ 64690-19-3 ]
YieldReaction ConditionsOperation in experiment
78.5% at 130℃; for 2 h; Large scale Into 200L reactor was pumped n-octylamine 100kg,30kg of 4-chloropyridine hydrochloride and 10kg of sodium fluoride were added, the temperature was raised to 130 ° C, and the mixture was stirred for 2 hours while keeping warm,Decompression recovery n-octylamine, while hot sodium carbonate aqueous solution to adjust the pH to about 7, adding ethyl acetate 120kg, separating the aqueous layer, the organic layer was cooled, filtered,Dried to give 4-octylaminopyridine 32.3kg,Purity was 99.3percent, yield was 78.5percent.
References: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596.
[2] Patent: CN107501173, 2017, A, . Location in patent: Paragraph 0018.
  • 4
  • [ 111-86-4 ]
  • [ 36316-71-9 ]
  • [ 64690-19-3 ]
References: [1] Angewandte Chemie - International Edition, 2005, vol. 44, # 9, p. 1371 - 1375.
  • 5
  • [ 15854-87-2 ]
  • [ 111-86-4 ]
  • [ 64690-19-3 ]
References: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596.
  • 6
  • [ 142-95-0 ]
  • [ 7379-35-3 ]
  • [ 64690-19-3 ]
YieldReaction ConditionsOperation in experiment
93% at 120 - 200℃; for 7 h; 5.0 g (0.0333 mol) of 4-chlororpyridine hydrochloride,And 0.55 g (0.0333 mol) of n-OCtylaminehydrochloride,The mixture is stirred and heated from 120 ° C to 180 ° C, heated to 200 ° C and held for 7 hours. The reaction was confirmed by thin-layer chromatography, and after completion, it was cooled and cooled to 100 ° C. To the reaction solution was added 20 ml of water and the mixture was cooled with stirring.To the reaction mixture was added 35percent aqueous solution of sodium hydroxide to make it alkaline. The mixture was extracted three times with 20 ml of di-dichloromethane (MC). The organic layer was collected, washed with 10 ml of cold water, washed with saturated brine, dehydrated with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure, 14 ml of hexane was added to the residue solid, and the mixture was refluxed and cooled. The resulting crystals were filtered, dried under reduced pressure at room temperature. [0103] 6.4 g of octylaminopyridine base (yield: 93.0percent, MP 65-69 ° C) was obtained through the above-mentioned procedure.
References: [1] Patent: KR2017/13425, 2017, A, . Location in patent: Paragraph 0099; 0100.
[2] Patent: US4206215, 1980, A, .
  • 7
  • [ 626-61-9 ]
  • [ 111-86-4 ]
  • [ 64690-19-3 ]
References: [1] Synlett, 2000, # 1, p. 116 - 118.
  • 8
  • [ 4783-86-2 ]
  • [ 142-95-0 ]
  • [ 64690-19-3 ]
References: [1] Doklady Chemistry, 1984, vol. 275, p. 97 - 100[2] Doklady Akademii Nauk SSSR, 1984, vol. 275, p. 385 - 387.
 

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