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[ CAS No. 65515-39-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 65515-39-1
Chemical Structure| 65515-39-1
Chemical Structure| 65515-39-1
Structure of 65515-39-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 65515-39-1 ]

CAS No. :65515-39-1 MDL No. :MFCD00124716
Formula : C9H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :WEJLKGQPSKTCBR-UHFFFAOYSA-N
M.W : 162.19 Pubchem ID :595276
Synonyms :

Calculated chemistry of [ 65515-39-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.38
TPSA : 45.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 1.58
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 2.22
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.18
Solubility : 1.06 mg/ml ; 0.00656 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 0.984 mg/ml ; 0.00607 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.0
Solubility : 0.161 mg/ml ; 0.000993 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 65515-39-1 ]

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 [ 65515-39-1 ]

* 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 [ 65515-39-1 ]
  • Downstream synthetic route of [ 65515-39-1 ]

[ 65515-39-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 14237-71-9 ]
  • [ 124-41-4 ]
  • [ 65515-39-1 ]
YieldReaction ConditionsOperation in experiment
100% for 1 h; Add a solution of NaOCH3 in MeOH (30 mass percent, 175 mL, 940 mmol) drop wise to a solution of 2-chloro-4,6-dimethyl-pyridine-3 -carbonitrile (75 g, 441.1 mmol) inMeOH (450 mL) in a water bath followed by another drop wise addition of NaOCH3 in MeOH (25 mass percent, 250 mL, 1090 mmol). Stir the resulting mixture for 1 hr, pour in ice cold water, stir for 30 mm, and filter the resulting solid. Wash filter cake with hexane and dry in a vacuum oven overnight. Extract the aqueous filtrate with DCM, dry the organic phase over Mg504, filter and concentrate in vacuo. Combine the filtered solid and theevaporated residue to afford title compound as a solid (71.8 g, quantitative yield). ES/MS (mlz): 163 (M+H).
99% at 0℃; for 10 h; 2-chloro-4,6-dimethyl-nicotinonitrile (2.5 g, 15.01 mmol) was dissolved in anhydrous methanol (70mL), added with sodium methoxide (4. 27 g, 75.03 mmol) at 0 °C and stirred for about 10 hours at nitrogen atmosphere. The above mixture was concentrated under reduced pressure and then neutrailized with a saturated solution of ammonium chloride and then extracted twice with 150 mL of methylenechloride. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (20percent EtOAc/Hexanes) was performed on the resulting residue and 2.41g (99percent) of 2- methoxy-4, 6-dimethyl-nicotinonitrile was obtained in white solid. 'H NMR (300 MHz, CDC13) 8 2.44 (s, 3H), 2.45 (s, 3H), 4.01 (s, 3H), 6.68 (s, 1H).
65% at 60℃; for 4 h; Step 2: 3-Cyano-4,6-dimethyl-2-methoxypyridine: A solution of 2-chloro-3-cyano-4,6- dimethylpyridine (4.60 g, 27.7 mmol) in methanol (30 mL) is added to a stirred solution of sodium methoxide (2.09 g, 38.78 mmol) in methanol (20 mL) and the reaction mixture is heated at 60°C for 4 hr. After cooling, the reaction is diluted with water (150 mL) and the solids are collected by filtration, washed with water and dried to yield 3-cyano-4,6-dimethyl-2- methoxypyridine (2.90 g, 65percent) as an off-white solid containing the same impurity as the starting material. LC/MS: MS m/e = 163 (M + H) ; RT 3.29 min; 1H NMR (CDCl3, 8 ppm) 6.69, (1H, s), 4.00 (3H, s), 2.43 (6H, s).
Reference: [1] Patent: WO2017/35060, 2017, A1, . Location in patent: Page/Page column 48; 49
[2] Patent: WO2005/63768, 2005, A1, . Location in patent: Page/Page column 33-34
[3] Patent: WO2005/97750, 2005, A1, . Location in patent: Page/Page column 75
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 331
  • 2
  • [ 67-56-1 ]
  • [ 14237-71-9 ]
  • [ 65515-39-1 ]
YieldReaction ConditionsOperation in experiment
100% at 70℃; for 4 h; Sodium (23 g, 0.99 mol) was added to dry MeOH (800 mL) portion-wise.
After the addition, the mixture was stirred for an hour until the sodium was mostly dissolved.
To the reaction mixture was added 2-chloro-4,6-dimethylpyridine-3-carbonitrile (110 g, 0.66 mol).
The resulting mixture was heated at 70° C. and stirred for four hours.
The suspension was filtered and the filtrate was concentrated under vacuum.
The residue was purified by column chromatography (petroleum ether/EtOAc, 10:1) to give 2-methoxy-4,6-dimethylpyridine-3-carbonitrile (Cpd S, 103 g, 100percent) as a white solid.
Reference: [1] Patent: US2014/179667, 2014, A1, . Location in patent: Paragraph 0786; 0787
  • 3
  • [ 14237-71-9 ]
  • [ 65515-39-1 ]
Reference: [1] Patent: EP104876, 1991, B1,
  • 4
  • [ 769-28-8 ]
  • [ 74-88-4 ]
  • [ 65515-39-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 9, p. 3446 - 3453
  • 5
  • [ 769-28-8 ]
  • [ 65515-39-1 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 331
  • 6
  • [ 14237-71-9 ]
  • [ 46002-83-9 ]
  • [ 65515-39-1 ]
Reference: [1] Patent: US2007/32529, 2007, A1,
  • 7
  • [ 18871-66-4 ]
  • [ 769-28-8 ]
  • [ 64038-03-5 ]
  • [ 65515-39-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
  • 8
  • [ 123-54-6 ]
  • [ 109-77-3 ]
  • [ 65515-39-1 ]
  • [ 769-28-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1982, # 11, p. 603 - 604
  • 9
  • [ 769-28-8 ]
  • [ 18871-66-4 ]
  • [ 64038-03-5 ]
  • [ 65515-39-1 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 11, p. 1763 - 1769
  • 10
  • [ 769-28-8 ]
  • [ 4637-24-5 ]
  • [ 64038-03-5 ]
  • [ 65515-39-1 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 11, p. 1763 - 1769
  • 11
  • [ 124-41-4 ]
  • [ 3102-33-8 ]
  • [ 109-77-3 ]
  • [ 65515-39-1 ]
  • [ 10272-10-3 ]
Reference: [1] Heterocycles, 1993, vol. 36, # 10, p. 2273 - 2280
  • 12
  • [ 65515-39-1 ]
  • [ 113893-02-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 9, p. 3446 - 3453
  • 13
  • [ 65515-39-1 ]
  • [ 1173081-96-3 ]
Reference: [1] Patent: US2014/179667, 2014, A1,
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