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Chemical Structure| 7584-05-6 Chemical Structure| 7584-05-6
Chemical Structure| 7584-05-6

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3-Methylisonicotinonitrile

CAS No.: 7584-05-6

4.5 *For Research Use Only !

Cat. No.: A275957 Purity: 98%

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Product Details of [ 7584-05-6 ]

CAS No. :7584-05-6
Formula : C7H6N2
M.W : 118.14
SMILES Code : CC1=C(C=CN=C1)C#N
MDL No. :MFCD09261048
Boiling Point : No data available
InChI Key :SFNWPKSTEHBXSY-UHFFFAOYSA-N
Pubchem ID :82063

Safety of [ 7584-05-6 ]

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

Calculated chemistry of [ 7584-05-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 33.92
TPSA ?

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

36.68 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.44
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

0.94
Log Po/w (WLOGP)?

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

1.26
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.

0.13
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

1.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.11

Water Solubility

Log S (ESOL):?

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

-1.66
Solubility 2.6 mg/ml ; 0.022 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.

-1.3
Solubility 5.96 mg/ml ; 0.0505 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

-2.45
Solubility 0.423 mg/ml ; 0.00358 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.

-6.35 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)

1.42

Application In Synthesis [ 7584-05-6 ]

* 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.

  • Downstream synthetic route of [ 7584-05-6 ]

[ 7584-05-6 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 1003-73-2 ]
  • [ 77-78-1 ]
  • [ 1620-77-5 ]
  • [ 7584-05-6 ]
  • [ 20970-75-6 ]
  • 2
  • [ 1003-73-2 ]
  • [ 74-88-4 ]
  • [ 7584-05-6 ]
  • [ 20970-75-6 ]
  • 3
  • [ 1681-36-3 ]
  • [ 7584-05-6 ]
  • 4
  • [ 7584-05-6 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 20002-31-7 ]
  • 5
  • [ 7584-05-6 ]
  • [ 4021-12-9 ]
  • 6
  • [ 151-50-8 ]
  • [ 86488-30-4 ]
  • [ 7584-05-6 ]
  • [ 20970-75-6 ]
  • 7
  • [ 1003-73-2 ]
  • [ 151-50-8 ]
  • [ 7584-05-6 ]
YieldReaction ConditionsOperation in experiment
34% Example 1; A. 3-Methyl-isonicotinonitrile.; To 3-methyl-pyridine 1 -oxide (15.90 g, 150 mmol) is added at 0 0C during 30 min. dimethylsulfate (15.60 mL). The resulting reaction mixture is stirred overnight at 40 0C. A solution of KCN (10.75 g, 165 mmol) in a mixture of EtOH/water 1 : 1 (120 mL) is added and the reaction mixture is stirred overnight at 40 0C. The reaction mixture is concentrated in vacuo and the residue is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc and the combined organic layers are dried over Na2SO4, filtered and concentrated at reduced pressure. Purification by flash column chromatography (silica gel, cyclohexane / EtOAc 85 : 15) affords the title compound as orange crystals (6.00 g, 50.80 mmol, 34%). 1H NMR (400 MHz, DMSO-(Z6) delta ppm 8.76 (s, 1 H), 8.64 (d, J = 4.9 Hz, 1 H), 7.80 (d, J = 4.9 Hz, 1 H).
34% 3-Methyl-isonicotinonitrile; To 3-methyl-pyridine 1 -oxide (15.9 g, 150 mmol) is added at 0 0C during 30 min. dimethylsulfate (15.6 ml_). The resulting reaction mixture is stirred overnight at 40 0C. A solution of KCN (10.75 g, 165 mmol) in a mixture of EtOH / water 1 : 1 (120 mL) is added and the reaction mixture is stirred overnight at 40 0C. The reaction mixture is concentrated in vacuo and the residue is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc and the combined organic layers are dried over Na2SO4, filtered and concentrated at reduced pressure. Purification by FCC (silica gel, cyclohexane / EtOAc 85 : 15) affords the title compound as orange crystals (6.0 g, 50.8 mmol, 34%). 1H NMR (400 MHz, DMSO-d6, 298 K): delta = 8.76 (s, 1 H), 8.64 (d, J = 4.9 Hz, 1 H), 7.80 (d, J = 4.9 Hz, 1 H).
A. A mixture of 3-methyl-pyridine 1-oxide (20 g, 0.183 mol) and iodoethane (32 mL, 0.403 mmol) is stirred 16 h. 200 mL water is added, the aqueous layer is separated and washed with Et2O. The collected aqueous layer is warmed to 50 C. and a solution of KCN (24 g, 0.366 mol) in 60 mL of water is added slowly in one hour. After an additional one hour stirring, the mixture is extracted with Et2O. The combined solvent is dried and concentrated to dryness. The residue is purified by silica gel column chromatography with hexanes:EtOAc=4:1 as eluent to provide 3-methyl-isonicotinonitrile.
  • 8
  • [ 3230-65-7 ]
  • [ 7584-05-6 ]
  • [ 131250-24-3 ]
  • 9
  • [ 67-56-1 ]
  • [ 7584-05-6 ]
  • 3-Methyl-isonicotinimidic acid methyl ester [ No CAS ]
  • 10
  • [ 7584-05-6 ]
  • [ 917-54-4 ]
  • [ 82352-00-9 ]
  • 11
  • [ 7584-05-6 ]
  • [ 4637-24-5 ]
  • [ 80935-76-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; for 120h; B. To a solution of <strong>[7584-05-6]3-methyl-isonicotinonitrile</strong> (12.25 g, 0.104 mmol) in 100 mL of DMF is added dimethylformamide dimethyl acetal (22 mL, 0.166 mol) portionwise in 5 days. The solvent is evaporated to dryness. The residue is purified by silica gel column chromatography with hexanes:EtOAc=4:1 as eluent to provide 3-(2-dimethylamino-vinyl)-isonicotinonitrile.
  • 12
  • [ 7584-05-6 ]
  • [ 2365-48-2 ]
  • [ 116986-03-9 ]
  • 13
  • [ 7584-05-6 ]
  • [ 103-63-9 ]
  • [ 113003-47-7 ]
  • 14
  • [ 151-50-8 ]
  • [ 87117-12-2 ]
  • [ 1620-77-5 ]
  • [ 7584-05-6 ]
  • [ 20970-75-6 ]
YieldReaction ConditionsOperation in experiment
The process in claim 63 in which the selected quaternary salt or its acid salt is of a first pyridine base from the group consisting of 4-cyanopyridine; 3-methyl-4-cyanopyridine; and 3-methylpyridine.
  • 18
  • [ 151-50-8 ]
  • [ 86488-30-4 ]
  • aqueous dioxane [ No CAS ]
  • [ 7584-05-6 ]
  • [ 20970-75-6 ]
  • 19
  • [ 151-50-8 ]
  • [ 87117-12-2 ]
  • aqueous dioxane [ No CAS ]
  • [ 1620-77-5 ]
  • [ 7584-05-6 ]
  • [ 20970-75-6 ]
  • 22
  • [ 7584-05-6 ]
  • [ 113003-48-8 ]
  • 23
  • [ 7584-05-6 ]
  • 1,3-Dimethyl-4-(3-phenyl)-propylpyridiniumiodid [ No CAS ]
  • 24
  • [ 7584-05-6 ]
  • [ 113018-67-0 ]
  • 25
  • [ 7584-05-6 ]
  • 3,4-Dihydro-1',3'-dimethylspiro<naphthalin-1(2H),4'-piperidin> [ No CAS ]
 

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