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Chemical Structure| 89809-63-2 Chemical Structure| 89809-63-2

Structure of 89809-63-2

Chemical Structure| 89809-63-2

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Product Details of [ 89809-63-2 ]

CAS No. :89809-63-2
Formula : C7H6N2O
M.W : 134.14
SMILES Code : COC1=CN=C(C=C1)C#N
MDL No. :MFCD08543467
InChI Key :XUGRSPXJFBZQSS-UHFFFAOYSA-N
Pubchem ID :13144279

Safety of [ 89809-63-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P280

Computational Chemistry of [ 89809-63-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 35.44
TPSA ?

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

45.91 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.59
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

0.88
Log Po/w (WLOGP)?

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

0.96
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.

-0.48
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

1.3
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.85

Water Solubility

Log S (ESOL):?

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

-1.6
Solubility 3.34 mg/ml ; 0.0249 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.43
Solubility 5.0 mg/ml ; 0.0373 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

-2.21
Solubility 0.837 mg/ml ; 0.00624 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.

-6.49 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

1.0
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)

1.83

Application In Synthesis of [ 89809-63-2 ]

* 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 [ 89809-63-2 ]

[ 89809-63-2 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 14906-61-7 ]
  • [ 7677-24-9 ]
  • [ 24059-89-0 ]
  • [ 89809-63-2 ]
  • 2
  • [ 327056-62-2 ]
  • [ 89809-63-2 ]
YieldReaction ConditionsOperation in experiment
304 mg (43%) In methanol; sodium methylate; A solution of 2-cyano-5-fluoropyridine (0.65 g, 5.3 mmol) in sodium methoxide (1.83 mL of 25% wt. solution in methanol, 7.95 mmol) was stirred at 0 C. for 1.5 hours and 2 hours at ambient temperature. The reaction was then diluted with ethyl acetate and washed with water and brine. Removal of the solvent in vacuo afforded 304 mg (43%) of 2-cyano-5-methoxypyridine.
  • 3
  • [ 89809-63-2 ]
  • [ 327056-65-5 ]
YieldReaction ConditionsOperation in experiment
79 mg (24%) With sodium hydroxide; hydroxylamine hydrochloride; In ethanol; Using the general procedure for the synthesis of amidoximes, <strong>[89809-63-2]2-cyano-5-methoxypyridine</strong> (270 mg, 2.01 mmol), a solution of hydroxylamine hydrochloride (0.457 ml of 5 M, 2.28 mmol) in ethanol (4 mL), and sodium hydroxide (0.230 mL of 10 N, 2.30 mmol) were heated at reflux for 24 hours. Standard work up afforded 79 mg (24%) of 5-methoxypyrid-2-ylamidoxime.
  • 4
  • 5-hydroxypyridine-2-carbonitrile [ No CAS ]
  • [ 74-88-4 ]
  • [ 89809-63-2 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 24h; To a mixture of 2-cyano-5-hydroxy pyridine (200 mg, 1.66 mmol), DMF (10 mL) and K2CO3 (253 mg, 1.83 mmol), was added MeI (354 mg, 2.49 mmol) at room temperature and the reaction mix was stirred for 24 h at room temperature. The reaction mix was poured into water and extracted with ethyl acetate. The organic layer was separated, washed with water, dried and concentrated to give 2-cyano-5-methoxy pyridine (175 mg, 78% yield).
  • 5
  • [ 89809-63-2 ]
  • [ 29082-92-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water;Heating / reflux; The <strong>[89809-63-2]2-cyano-5-methoxy pyridine</strong> (170 mg, 1.26 mmol) was taken into 6N HCI (4 mL) and refluxed for 16 hours. The reaction mix was cooled to room temperature and diluted with water, neutralized, and extracted with ethyl acetate. The organic layer was washed with water, then brine, and was dried and concentrated to give crude 5-methoxy-2-nicotinic acid (290 mg).
  • 6
  • [ 89809-63-2 ]
  • 5-(methyloxy)-2-pyridinecarboximidamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a suspension of <strong>[89809-63-2]5-(methyloxy)-2-pyridinecarbonitrile</strong> (3 g, 22.4 mmol) in dry EtOH (35 mL) was added NaOMe (0.12 g, 2.24 mmol). The resulting mixture was stirred at room temperature for 17 hr. Ammonium chloride (1 .56 g, 29.1 mmol) was added then the resulting mixture refluxed for 1 hr. The mixture was allowed to cool to room temperature then concentrated under reduced pressure to give the crude product as a brown solid. The crude product was triturated with diethyl ether and the resulting suspension filtered under vacuum then dried at 40C under vacuum to give the title compound as an orange solid (4.3g). LCMS (Method B): Rt = 0.49min, MH+ 152.0
  • 11
  • [ 89809-63-2 ]
  • 5-hydroxypyridine-2-carbonitrile [ No CAS ]
  • 12
  • [ 89809-63-2 ]
  • [ 1578264-74-0 ]
  • [ 1578264-75-1 ]
  • 13
  • [ 557-21-1 ]
  • [ 139585-48-1 ]
  • [ 89809-63-2 ]
  • 14
  • [ 41288-96-4 ]
  • [ 89809-63-2 ]
  • 15
  • [ 89809-63-2 ]
  • 2 [ No CAS ]
  • 5-methoxypyridine-2-carboximidamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g To a solution of 5-methyoxypyridine-2-carbonitrile (1.0 g, 7.46 mmol) in methanol (20 mL)was added NaOCH3 (80 mg, 1.49 mmol). The mixture was stuffed at rt for 12 hrs. Then to thereaction mixture was added NH4C1 (399 mg, 7.46 mmol). After being heated under reflux for 3 hrs, the reaction mixture was then concentrated in vacuo. The residue was suspended in ethanol (30 mL) and the suspension was heated under reflux for 1 hr. The resulting mixture was filtered and the filtrate was concentrated in vacuo to afford 5-metyoxypyridine-2-carboxarnidinehydrochloride (1.3 g), which was used in the next step without further purification.
  • 16
  • [ 136030-00-7 ]
  • [ 89809-63-2 ]
  • (3aR,8aS)-2-(5-methoxypyridin-2-yl)-8,8a-dihydro-3aH-indeno[1,2-d]oxazole [ No CAS ]
  • 17
  • [ 89809-63-2 ]
  • (Z)-N'-hydroxy-5-methoxypicolinimidamide [ No CAS ]
  • 18
  • [ 89809-63-2 ]
  • 5-isopropyl-3-(5-methoxypyridin-2-yl)-1,2,4-oxadiazole [ No CAS ]
  • 19
  • [ 89809-63-2 ]
  • 6-(5-isopropyl-1,2,4-oxadiazol-3-yl)pyridin-3-ol [ No CAS ]
  • 20
  • [ 89809-63-2 ]
  • 4-((6-(5-isopropyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl)oxy)-N-methylpicolinamide [ No CAS ]
 

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