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[ CAS No. 166526-03-0 ] {[proInfo.proName]}

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Chemical Structure| 166526-03-0
Chemical Structure| 166526-03-0
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Product Details of [ 166526-03-0 ]

CAS No. :166526-03-0 MDL No. :MFCD08276124
Formula : C6H2Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :VNRGFXKFARXGSX-UHFFFAOYSA-N
M.W : 173.00 Pubchem ID :45588080
Synonyms :

Calculated chemistry of [ 166526-03-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.97
TPSA : 36.68 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) : -5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 2.61
Consensus Log Po/w : 1.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.332 mg/ml ; 0.00192 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.473 mg/ml ; 0.00274 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.34
Solubility : 0.0793 mg/ml ; 0.000458 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 166526-03-0 ]

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

Application In Synthesis of [ 166526-03-0 ]

* 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 [ 166526-03-0 ]
  • Downstream synthetic route of [ 166526-03-0 ]

[ 166526-03-0 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 166526-03-0 ]
  • [ 55934-01-5 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 2
  • [ 166526-03-0 ]
  • [ 7321-93-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 3
  • [ 166526-03-0 ]
  • [ 405230-82-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 4
  • [ 70593-57-6 ]
  • [ 166526-03-0 ]
YieldReaction ConditionsOperation in experiment
88% With pyridine; trichlorophosphate In acetonitrile at 20 - 60℃; for 1.5 h; 4,6-Dichloro-nicotinonitrile (3) (1175) Pyridine (20.3 mL, 250 mmol) was added to a suspension of 4,6-dichloro-nicotinamide (8.00 g, 41.9 mmol) in acetonitrile (180 mL) at room temperature POCl3 (11.7 mL, 126 mmol) was added over 3 minutes at room temperature. The reaction mixture was heated at 60° C. with for 1.5 hours. The reaction solution was cooled to room temperature and poured into aqueous NaOH (0.8M, 600 mL) followed by extraction with EtOAc (6×400 mL). The organic extracts were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash column chromatography (30percent ethyl acetate/hexanes) to give the title compound as a light orange solid (6.41 g, 88percent) 1H NMR 400 MHz (CDCl3) 88.67 (s, 1H), 7.58 (s, 1H).
Reference: [1] Patent: US2015/291629, 2015, A1, . Location in patent: Paragraph 1175
  • 5
  • [ 5466-62-6 ]
  • [ 166526-03-0 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5444
  • 6
  • [ 73027-79-9 ]
  • [ 166526-03-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
[2] Patent: US2015/291629, 2015, A1,
  • 7
  • [ 40296-46-6 ]
  • [ 166526-03-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 8
  • [ 6975-44-6 ]
  • [ 166526-03-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 9
  • [ 166526-03-0 ]
  • [ 28443-69-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  • 10
  • [ 166526-03-0 ]
  • [ 124-41-4 ]
  • [ 1187190-69-7 ]
YieldReaction ConditionsOperation in experiment
77% at 60℃; 6-Chloro-4-methoxy-nicotinonitrile (2) (1104) To a solution of 4,6-dichloro-nicotinonitrile (1) (200 mg, 1.06 mmol) in methanol (anhydrous, 10 mL) was added sodium methoxide solution (0.5 M/MeOH, 2.12 mL, 1.06 mmol). The reaction was heated at 60° C. overnight. After cooling the reaction solution to room temperature, HCl (1M, 8 mL) was added. The volatile components were evaporated in vacuo. Purification was accomplished by Biotage (10percent-50percent EtOAc/hexanes gradient mobile phase) to afford 150 mg (77percent yield) of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.48 (s, 1H), 6.98 (s, 1H), 4.03 (s, 3H)
Reference: [1] Patent: US2015/291629, 2015, A1, . Location in patent: Paragraph 1104
  • 11
  • [ 67-56-1 ]
  • [ 166526-03-0 ]
  • [ 1187190-69-7 ]
YieldReaction ConditionsOperation in experiment
72% at 17 - 25℃; for 1 h; Inert atmosphere 4,6-Dichioronicotinonitrile (0.10 g, 0.58 mmol) was added to a suspension of potassiumcarbonate (0.080 g, 0.58 mmol) in MeOH (5 mL). The resulting mixture was stirred at roomtemperature for 1 hour and then concentrated under reduced pressure. The resulting residuewas extracted with methylene chloride, and the organic layer was concentrated underreduced pressure. The resulting residue was purified by flash silica chromatography, elutiongradient 0 to 50percent ethyl acetate in hexanes, to afford 6-chloro-4-methoxynicotinonitrile(0.070 g, 72percent) as a white solid. ‘H NMR (DMSO-d6, 27 °C) 4.04 (3H, s), 7.52 (1H, s), 8.71(1H, s). mlz: ES+ [M+H]+ 169.
Reference: [1] Patent: WO2018/19793, 2018, A1, . Location in patent: Page/Page column 166; 167
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