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[ CAS No. 52689-19-7 ] {[proInfo.proName]}

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Chemical Structure| 52689-19-7
Chemical Structure| 52689-19-7
Structure of 52689-19-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 52689-19-7 ]

CAS No. :52689-19-7 MDL No. :MFCD13189084
Formula : C8H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :HLPONRCXYZPNFJ-UHFFFAOYSA-N
M.W : 146.15 Pubchem ID :23103747
Synonyms :

Calculated chemistry of [ 52689-19-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.15
TPSA : 53.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 0.59
Log Po/w (WLOGP) : 1.16
Log Po/w (MLOGP) : -0.51
Log Po/w (SILICOS-IT) : 1.62
Consensus Log Po/w : 0.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.46
Solubility : 5.12 mg/ml ; 0.035 mol/l
Class : Very soluble
Log S (Ali) : -1.29
Solubility : 7.46 mg/ml ; 0.051 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.42
Solubility : 0.549 mg/ml ; 0.00376 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 52689-19-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52689-19-7 ]

* 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 [ 52689-19-7 ]
  • Downstream synthetic route of [ 52689-19-7 ]

[ 52689-19-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 928649-93-8 ]
  • [ 52689-19-7 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 16 h;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water
6-Acetyl-nicotinonitrile; Dissolve crude 6-(l-ethoxy-vinyl)-nicotinonitrile (14.5 g, ca. 80percent) in THF (120 mL) and 2.5 N hydrochloric acid (40 mL). Stir the solution for 16 h at room temperature. Quench the reaction with saturated aqueous NaHCO3 (pH to 7.5). Extract the mixture with EtOAc (200 mL). Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g) eluting with hexane/EtOAc (9:1 to 3:1 gradient) to obtain the desired intermediate (4.2 g, 65percent).
Reference: [1] Patent: WO2007/28083, 2007, A2, . Location in patent: Page/Page column 142
  • 2
  • [ 100-54-9 ]
  • [ 127-17-3 ]
  • [ 52689-19-7 ]
YieldReaction ConditionsOperation in experiment
21%
Stage #1: With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; water at 0 - 40℃; for 1.5 h;
Stage #2: With sodium hydroxide In dichloromethane; water at 0℃;
Method B; 1) 2-Acetyl-5-cyanopyridine; Ammonium peroxodisulfate (10.3 g) was gradually added to a solution of 3-cyanopyridine (3.12 g), pyruvic acid (6.23 ml), and silver nitrate (1.27 g) in a mixture of dichloromethane (150 ml) and water (150 ml) at room temperature. Sulfuric acid (3.2 ml) was gradually added to the reaction liquid under ice cooling, and the mixture was stirred at 40°C for 1.5 hours. To the reaction liquid was added 1N aqueous sodium hydroxide to make the solution basic under ice cooling, and the solution was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate-hexane) to give 2-acetyl-5-cyanopyridine (903 mg, 21percent) as a solid. 1H-NMR (400 MHz, CDCl3)δ: 2.75 (3H, s), 8.13-8.16 (2H, m), 8.95 (1H, d, J = 1.2 Hz).
21%
Stage #1: With ammonium peroxydisulfate; silver nitrate In dichloromethane; water
Stage #2: With sulfuric acid In dichloromethane; water at 0 - 40℃; for 1.5 h;
Stage #3: With sodium hydroxide In dichloromethane; water
1)
2-Acetyl-5-cyanopyridine
At room temperature, ammonium peroxodisulfate (10.3 g) was gradually added to 3-cyanopyridine (3.12 g), pyruvic acid (6.23 mL), and silver nitrate (1.27 g) in a mixture of dichloromethane (150 mL) and water (150 mL).
Sulfuric acid (3.2 mL) was gradually added to the reaction mixture under cooling on ice, followed by stirring at 40°C for 1.5 hours.
Subsequently, the reaction mixture was alkalinized with 1M aqueous solution of sodium hydroxide under cooling on ice, and then the resultant mixture was extracted with dichloromethane.
The organic layer was dried over sodium sulfate anhydrate.
After a filtration step, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate - hexane), to thereby give 2-acetyl-5-cyanopyridine as a solid product (903 mg, 21percent).
1H-NMR(400MHz,CDCl3)δ:2.75(3H,s), 8.13-8.16(2H,m), 8.95(1H,d,J=1.2Hz).
21%
Stage #1: With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; water at 0 - 40℃; for 1.5 h;
Stage #2: With sodium hydroxide In dichloromethane; water at 0℃;
1) 2-Acetyl-5-cyanopyridine Ammonium peroxodisulfate (10.3 g) was slowly added to a mixture of 3-cyanopyridine (3.12 g), pyruvic acid (6.23 mL) and silver nitrate (1.27 g) in dichloromethane (150 mL) and water (150 mL) at room temperature. Under ice cooling, sulfuric acid (3.2 mL) was slowly added to the reaction solution, and then the mixture was stirred for 1.5 hours at 40°C. Under ice cooling, the reaction solution was alkalinized by adding an aqueous 1 M sodium hydroxide solution, and then extracted with dichloromethane. The organic solvent was dried over anhydrous sodium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane-ethyl acetate), to obtain 2-acetyl-5-cyanopyridine (903 mg, 21percent) as a solid. 1H-NMR(400MHz, CDCl3)δ: 2.75(3H, s), 8.13-8.16(2H, m), 8.95(1H, d, J=1.2Hz).
Reference: [1] Patent: EP1698626, 2006, A1, . Location in patent: Page/Page column 86-87
[2] Patent: EP1762568, 2007, A1, . Location in patent: Page/Page column 29
[3] Patent: EP1785418, 2007, A1, . Location in patent: Page/Page column 76
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