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[ CAS No. 65610-13-1 ] {[proInfo.proName]}

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Chemical Structure| 65610-13-1
Chemical Structure| 65610-13-1
Structure of 65610-13-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 65610-13-1 ]

CAS No. :65610-13-1 MDL No. :MFCD00052458
Formula : C8H3FN2 Boiling Point : -
Linear Structure Formula :- InChI Key :SAPTYURANIHAPE-UHFFFAOYSA-N
M.W : 146.12 Pubchem ID :11960964
Synonyms :

Calculated chemistry of [ 65610-13-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.83
TPSA : 47.58 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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 1.2
Log Po/w (SILICOS-IT) : 2.19
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.07
Solubility : 1.25 mg/ml ; 0.00852 mol/l
Class : Soluble
Log S (Ali) : -2.07
Solubility : 1.26 mg/ml ; 0.0086 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.218 mg/ml ; 0.00149 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 65610-13-1 ]

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 [ 65610-13-1 ]

* 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 [ 65610-13-1 ]
  • Downstream synthetic route of [ 65610-13-1 ]

[ 65610-13-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 77326-36-4 ]
  • [ 151-50-8 ]
  • [ 65610-13-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1357 - 1364
  • 2
  • [ 65610-13-1 ]
  • [ 1240518-54-0 ]
YieldReaction ConditionsOperation in experiment
87% With hydrazine hydrate In ethanol at 70℃; Intermediate 623-Amino-1H-indazole-4-carbonitrile; 3-Fluoro-1,2-benzenedicarbonitrile (APIN) (5 g, 34.2 mmol) was dissolved in ethanol (80 mL) and hydrazine monohydrate (4.98 mL, 103 mmol) was added to the solution. The reaction was heated at 70° C. overnight. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with water (100 mL). The aqueous layers were extracted with ethyl acetate (200 mL). Organic layers were combined, dried over anhydrous magnesium sulfate and evaporated in vacuo to give the title compound (4.7 g, 87percent) as a yellow solid. LCMS (System A) RT=0.53 min, ES+ve m/z 159 (M+H)+.
47% With hydrazine hydrate In ethanol at 70℃; for 8 h; 3-Fluorophthalonitrile (1.00 g, 6.84 mmol) was dissolved in ethanol (10 mL) and treated with hydrazine hydrate (1.37 g, 27.4 mmol). After stirring at 70 °C for 8 h, the mixture was cooled to RT and concentrated in vacuo. The residue was dissolved in a mixture of water and ethyl acetate. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with water and with brine, dried over magnesium sulfate, concentrated in vacuo and dried to yield the title compound (0.51 g, 47percent of theory) LC-MS (Method 2B): Rt = 1.47 min, MS (ESIPos): m/z = 159 [M+H]+
0.51 g With hydrazine hydrate In ethanol at 70℃; for 8 h; Example 77A
3-Amino-1H-indazole-4-carbonitrile
3-Fluorophthalonitrile (1.00 g, 6.84 mmol) was dissolved in ethanol (10 mL) and treated with hydrazine hydrate (1.37 g, 27.4 mmol).
After stirring at 70° C. for 8 h, the mixture was cooled to RT and concentrated in vacuo.
The residue was dissolved in a mixture of water and ethyl acetate.
The aqueous layer was extracted once more with ethyl acetate.
The combined organic layers were washed with water and with brine, dried over magnesium sulfate, concentrated in vacuo and dried to yield the title compound (0.51 g, 47percent of theory)
LC-MS (Method 2B): Rt=1.47 min, MS (ESIPos): m/z=159 [M+H]+
Reference: [1] Patent: US2010/216860, 2010, A1, . Location in patent: Page/Page column 32
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1946 - 1960
[3] Patent: WO2015/67549, 2015, A1, . Location in patent: Page/Page column 105
[4] Patent: US2015/126449, 2015, A1, . Location in patent: Paragraph 0578 - 0580
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