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[ CAS No. 65189-15-3 ] {[proInfo.proName]}

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Chemical Structure| 65189-15-3
Chemical Structure| 65189-15-3
Structure of 65189-15-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 65189-15-3 ]

CAS No. :65189-15-3 MDL No. :MFCD11100247
Formula : C6H2Cl2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :JBMLYEZUHCZNKT-UHFFFAOYSA-N
M.W : 173.00 Pubchem ID :12878464
Synonyms :

Calculated chemistry of [ 65189-15-3 ]      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) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.55
Log Po/w (XLOGP3) : 2.2
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) : -2.74
Solubility : 0.313 mg/ml ; 0.00181 mol/l
Class : Soluble
Log S (Ali) : -2.6
Solubility : 0.43 mg/ml ; 0.00249 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 : 1.84

Safety of [ 65189-15-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65189-15-3 ]

* 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 [ 65189-15-3 ]
  • Downstream synthetic route of [ 65189-15-3 ]

[ 65189-15-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 75291-84-8 ]
  • [ 65189-15-3 ]
YieldReaction ConditionsOperation in experiment
78% With thionyl chloride In neat (no solvent) for 72 h; Reflux Intermediate 1 (8.4 g, 44 mmol) is suspended in 76 mL of thionyl chloride. The reaction mixture is stirred under reflux for 72h. The solvent is reduced under vacuum and the residue is dissolved in chloroform. The organic layer is washed with water and dried over anhydrous sodium sulfate. After reducing the solvent under vacuum, the solid is first purified via column chromatography (reversed phase, eluent: acetonitrile/dichloromethane) and then crystallized in ethyl acetate to give the title product in 78percent yield (5.95 g). H-NMR (CDCI3): δ = 8.05 (s, 1 H), 8.60 (s, 1 H).
Reference: [1] Patent: WO2015/150203, 2015, A1, . Location in patent: Page/Page column 74
  • 2
  • [ 79-37-8 ]
  • [ 41667-95-2 ]
  • [ 65189-15-3 ]
YieldReaction ConditionsOperation in experiment
27% With thionyl chloride; ammonia In tetrahydrofuran; <i>N</i>-methyl-acetamide; methanol; dichloromethane a)
5,6-Dichloro-pyridine-3-carbonitrile

To a stirred solution of 5,6-dichloro-pyridine-3-carboxylic acid (1.11 mg, 5.79 mmol) and methylene chloride (1.5 mL) in an ice bath under argon was added oxalyl chloride (4.4 mL, 8.8 mmol) over 25 min followed by 2 drops of dimethylformamide.
The solution was stirred for 5 min, the ice bath was removed, and the solution was stirred for 1.5 h.
The solution was concentrated to yield a white solid.
To the solid was added tetrahydrofuran (5.0 mL) and 7 N ammonia in methanol (4.0 mL, 28.0 mmol).
The solution was stirred for 1 min and then partitioned between deionized water (25 mL) and 1:1 dichloromethane:ethyl acetate (3*50 mL).
The organic layers were concentrated.
To the solid was added thionyl chloride (50 mL) and the solution was refluxed under argon for 69 h.
The solution was concentrated and the residue was purified twice by column chromatography (1:2, hexane:ethyl acetate, then by 1:1, hexane:ethyl acetate) to yield 268 mg (27percent) of the title compound. 1H NMR (CDCl3): 8.59 (d, J=2.20 Hz, 1H), 8.05 (d, J=2.20 Hz, 1H).
Reference: [1] Patent: US2003/45546, 2003, A1,
  • 3
  • [ 1256794-26-9 ]
  • [ 65189-15-3 ]
Reference: [1] Patent: WO2006/88840, 2006, A1, . Location in patent: Page/Page column 108-109
  • 4
  • [ 41667-95-2 ]
  • [ 65189-15-3 ]
Reference: [1] Patent: WO2015/150203, 2015, A1,
  • 5
  • [ 65189-15-3 ]
  • [ 41667-95-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 127,129
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