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[ CAS No. 5825-71-8 ] {[proInfo.proName]}

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Chemical Structure| 5825-71-8
Chemical Structure| 5825-71-8
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Product Details of [ 5825-71-8 ]

CAS No. :5825-71-8 MDL No. :MFCD06411548
Formula : C11H10N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :NZJIUQJPKXRRHB-UHFFFAOYSA-N
M.W : 234.21 Pubchem ID :2794621
Synonyms :

Calculated chemistry of [ 5825-71-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.18
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.75
TPSA : 69.9 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 1.1
Log Po/w (WLOGP) : 0.91
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 0.66
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.11
Solubility : 1.81 mg/ml ; 0.00771 mol/l
Class : Soluble
Log S (Ali) : -2.16
Solubility : 1.62 mg/ml ; 0.00691 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.25
Solubility : 1.33 mg/ml ; 0.00568 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 5825-71-8 ]

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 [ 5825-71-8 ]

* 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 [ 5825-71-8 ]
  • Downstream synthetic route of [ 5825-71-8 ]

[ 5825-71-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5825-71-8 ]
  • [ 63237-88-7 ]
YieldReaction ConditionsOperation in experiment
81% at 80℃; for 2.5 h; Reference Example 43-1
(R)-2-methyl-N-((R)-1-(pyrazolo[1,5-a]pyridin-2-yl)ethyl)propane-2-sulfinamide
Pyrazolo[1,5-a]pyridine-2,3-dicarboxylic acid dimethyl ester (3.35 g, 14 mmol) was dissolved in 50percent sulfuric acid (110 mL), and the solution was stirred for 2.5 hours at 80°C.
The reaction liquid was cooled to 0°C, and a 8 M aqueous solution of sodium hydroxide was added thereto to adjust the pH to 9.
Subsequently, the pH was adjusted to 3 with 6 M hydrochloric acid.
A suspension liquid thus produced was separated by filtration, and crystals were washed with water and then dried under reduced pressure.
Thus, pyrazolo[1,5-a]pyridine-2-carboxylic acid (pale brown crystals, 1.88 g, 81percent) was obtained.
In a nitrogen atmosphere, pyrazolo[1,5-a]pyridine-2-carboxylic acid (941 mg, 5.8 mmol) thus obtained was dissolved in THF (30 mL), and the solution was stirred for a while at room temperature. Subsequently, a THF solution of a borane-THF complex (20 mL, 18 mmol, 0.9 M) was added to the solution, and the mixture was stirred for 3.5 hours at 70°C. The reaction liquid was cooled to 0°C, water was added thereto, and the mixture was stirred for a while. Subsequently, 6 N hydrochloric acid was added thereto, and the mixture was heated to reflux for one hour. The solvent was distilled off under reduced pressure, subsequently methanol was added thereto, and the solvent was distilled off again. A residue thus obtained was diluted with ethyl acetate, and the organic layer was washed with a 1 N aqueous solution of sodium hydroxide, water, and saturated brine. The organic layer was dried over anhydrous sodium sulfate, insoluble matters were filtered, and then the solvent was distilled off under reduced pressure. Thus, pyrazolo[1,5-a]pyridin-2-ylmethanol was obtained. According to a technique similar to that of Reference Example 13-3, pyrazolo[1,5-a]pyridine-2-carboaldehyde was obtained using pyrazolo[1,5-a]pyridin-2-ylmethanol thus obtained. According to a technique similar to that of Reference Example 1-2, (R)-2-methyl-N-(pyrazolo[1,5-a]pyridin-2-ylmethylene)propane-2-sulfinamide was obtained using pyrazolo[1,5-a]pyridine-2-carboaldehyde thus obtained and (R)-2-methylpropane-2-sulfinamide. According to a technique similar to that of Reference Example 1-3, the title compound (pale yellow oily material, 498 mg, 65percent) was obtained using (R)-2-methyl-N-(pyrazolo[1,5-a]pyridin-2-ylmethylene)propane-2-sulfinamide thus obtained.
Reference: [1] Patent: EP3404021, 2018, A1, . Location in patent: Paragraph 0224
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 17, p. 2691 - 2694
[3] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1149 - 1152
[4] Patent: WO2015/66371, 2015, A1,
[5] Patent: CN107778310, 2018, A, . Location in patent: Paragraph 0044; 0045
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