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[ CAS No. 131666-74-5 ] {[proInfo.proName]}

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Chemical Structure| 131666-74-5
Chemical Structure| 131666-74-5
Structure of 131666-74-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 131666-74-5 ]

CAS No. :131666-74-5 MDL No. :MFCD20527514
Formula : C10H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :GJIMTGCSEXYRCB-UHFFFAOYSA-N
M.W : 190.20 Pubchem ID :14458625
Synonyms :

Calculated chemistry of [ 131666-74-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.96
TPSA : 54.98 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) : -6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.38
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.3 mg/ml ; 0.00682 mol/l
Class : Soluble
Log S (Ali) : -2.14
Solubility : 1.38 mg/ml ; 0.00728 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0768 mg/ml ; 0.000404 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 131666-74-5 ]

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

Application In Synthesis of [ 131666-74-5 ]

* 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 [ 131666-74-5 ]
  • Downstream synthetic route of [ 131666-74-5 ]

[ 131666-74-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 26663-42-3 ]
  • [ 131666-74-5 ]
YieldReaction ConditionsOperation in experiment
93% at 68℃; for 16 h; To a stirred solution of 2-(1H-indazol-3-yl)acetic acid (35-1) (4.86 g, 27.5 mmol) in Methanol (250 mL ) was added sulfuric acid (0.543 g, 5.53 mmol) and the reaction was refluxed at 68°C for 16 h. Reaction progress was monitored by TLC. The MeOH was evaporated to dryness and the residual gum was basified with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and evaporated in vacuo to yield methyl 2-(1H-indazol-3-yl)acetate (35-2) (4.90 g, 25.7 mmol, 93 percent) as a light brown solid.
77% for 14 h; Reflux General procedure: A solution of the (2-aza-)indoleacetic acid derivative (1 equivalent) in alcohol (preferentially methanol; 8.8 mL/mmol) containing 3 drops/mmol of concentrated sulfuric acid is refluxed overnight until the starting material is consumed. The progress of the conversion is monitored by TLC and/or LCMS. The reaction mixture is concentrated under reduced pressure to a low volume, and then diluted with ethyl acetate (5 mL/mmol). The organic layer is treated with water (2x3 mL/mmol) and 10percent sodium bicarbonate solution (3 mL). The ethyl acetate phase is collected, dried over sodium sulfate, concentrated and then kept at high vacuum to obtain the title compound as an amorphous solid.
Reference: [1] Patent: WO2017/197046, 2017, A1, . Location in patent: Page/Page column 328
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
[3] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058,10
[4] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058
[5] Tetrahedron, 2012, vol. 68, # 49, p. 10180 - 10187
[6] Patent: WO2013/59245, 2013, A1, . Location in patent: Page/Page column 64
  • 2
  • [ 26663-42-3 ]
  • [ 131666-74-5 ]
Reference: [1] Patent: US4954629, 1990, A,
[2] Patent: EP325375, 1989, A1,
  • 3
  • [ 174180-42-8 ]
  • [ 131666-74-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
  • 4
  • [ 101714-15-2 ]
  • [ 131666-74-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7344 - 7350
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