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[ CAS No. 74960-46-6 ] {[proInfo.proName]}

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Chemical Structure| 74960-46-6
Chemical Structure| 74960-46-6
Structure of 74960-46-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 74960-46-6 ]

CAS No. :74960-46-6 MDL No. :MFCD22126114
Formula : C9H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZJPXWLZSUROYHX-UHFFFAOYSA-N
M.W : 176.60 Pubchem ID :66545122
Synonyms :

Calculated chemistry of [ 74960-46-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.02
TPSA : 39.58 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) : -5.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 3.11
Consensus Log Po/w : 2.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.21
Solubility : 0.109 mg/ml ; 0.000617 mol/l
Class : Soluble
Log S (Ali) : -3.22
Solubility : 0.108 mg/ml ; 0.000609 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.98
Solubility : 0.0184 mg/ml ; 0.000104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 74960-46-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 74960-46-6 ]

* 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.

  • Upstream synthesis route of [ 74960-46-6 ]
  • Downstream synthetic route of [ 74960-46-6 ]

[ 74960-46-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 942433-61-6 ]
  • [ 74960-46-6 ]
YieldReaction ConditionsOperation in experiment
82.1% With trichlorophosphate In chloroform for 3 h; Reflux A mixture of 28.05 g (144 mmol) of 3-chloro-lH-indole-2-carboxylic acid amide, 67.36 mL (722 mmol) of phosphorus oxychloride and 525 mL of chloroform was refluxed for 3h. The reaction mixture was cooled to 20 °C, poured into a mixture of 40 mL of 37 percent hydrochloric acid and 1000 g of ice, then stirred for 2 h. The organic layer was separated and the water phase was extracted with 500 mL of chloroform. The combined organic layers were washed with water and saturated sodium carbonate solution, dried over anhydrous sodium sulfate and concentrated. The residue was crystallized from a 1 :1 mixture of 2-propanol and water to yield 20.89 g (82.1 percent) of the title compound. Mp.: 150-154°C.
82.1%
Stage #1: With trichlorophosphate In chloroform; water for 3 h; Reflux
Stage #2: With hydrogenchloride In water at 20℃; for 2 h; Cooling with ice
c)
3-Chloro-1H-indole-2-carbonitrile
A mixture of 28.05 g (144 mmol) of 3-chloro-1H-indole-2-carboxylic acid amide, 67.36 mL (722 mmol) of phosphorus oxychloride and 525 mL of chloroform was refluxed for 3 h.
The reaction mixture was cooled to 20° C., poured into a mixture of 40 mL of 37percent hydrochloric acid and 1000 g of ice, then stirred for 2 h.
The organic layer was separated and the water phase was extracted with 500 mL of chloroform.
The combined organic layers were washed with water and saturated sodium carbonate solution, dried over anhydrous sodium sulfate and concentrated.
The residue was crystallized from a 1:1 mixture of 2-propanol and water to yield 20.89 g (82.1percent) of the title compound. Mp.: 150-154° C.
Reference: [1] Patent: WO2012/59776, 2012, A1, . Location in patent: Page/Page column 38
[2] Patent: US2013/217702, 2013, A1, . Location in patent: Paragraph 0116
  • 2
  • [ 28737-32-8 ]
  • [ 74960-46-6 ]
Reference: [1] Patent: WO2012/59776, 2012, A1,
[2] Patent: US2013/217702, 2013, A1,
  • 3
  • [ 1477-50-5 ]
  • [ 74960-46-6 ]
Reference: [1] Patent: WO2012/59776, 2012, A1,
[2] Patent: US2013/217702, 2013, A1,
  • 4
  • [ 74960-45-5 ]
  • [ 62542-45-4 ]
  • [ 74960-46-6 ]
  • [ 74960-48-8 ]
  • [ 74960-62-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 4, p. 1157 - 1171
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