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[ CAS No. 106778-43-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 106778-43-2
Chemical Structure| 106778-43-2
Chemical Structure| 106778-43-2
Structure of 106778-43-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 106778-43-2 ]

CAS No. :106778-43-2 MDL No. :MFCD09910323
Formula : C10H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ADAHADRJWVCICR-UHFFFAOYSA-N
M.W : 173.17 Pubchem ID :22128831
Synonyms :

Calculated chemistry of [ 106778-43-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.7
TPSA : 50.19 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) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.57

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.54
Solubility : 0.501 mg/ml ; 0.0029 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.611 mg/ml ; 0.00353 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.147 mg/ml ; 0.000851 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 106778-43-2 ]

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 [ 106778-43-2 ]

* 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 [ 106778-43-2 ]
  • Downstream synthetic route of [ 106778-43-2 ]

[ 106778-43-2 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 106778-42-1 ]
  • [ 106778-43-2 ]
YieldReaction ConditionsOperation in experiment
21%
Stage #1: With potassium hydroxide In diethylene glycol at 160℃; for 3 h;
Stage #2: With hydrogenchloride In water; diethylene glycol
Preparation Example G-1. Isoquinoline-6-carboxylic acid A solution prepared by adding (4-bromobenzylydene)-(2,2-diethoxyethyl) amine (synthesized from 4-bromobenzaldehyde, according to the method described in J. Org. Chem., vol. 48, 3344-3346 (1983)) (51.4g, 0.189mmol) to an ice-cold concentrated sulfuric acid (20g) was added to a solution prepared by adding diphosphorus pentoxide (40g) to an ice-cold concentrated sulfuric acid (360g), and the solution was stirred at 160°C for 2 hours. The reaction solution was gradually cooled to 0°C, the solution was filtered through Celite pad, the filtrate was neutralized with sodium carbonate. This solution was further filtrated through Celite pad, this filtrate was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 6-bromoisoquinoline (482mg, 1.2percent) was obtained as an orange oil. Next, to a solution of 6-bromoisoquinoline (382mg, 1.84mmol) in N,N-dimethylformamide (3.8mL) were added zinc cyanide (431 mg, 3.67mmol) and tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) under nitrogen atmosphere, and the mixture was stirred at 100°C for 1 hour. Tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) was further added, and the mixture was stirred for 2.5 hours at 100°C. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for extraction, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (hexane : ethyl acetate), and isoquinoline-6-carbonitrile (234mg, 83percent) was obtained as a yellow solid. Lastly, isoquinoline-6-carbonitrile (51mg, 0.331 mmol) was dissolved in diethyleneglycol (1.0mL), potassium hydroxide (9mg, 0.166mmol) was added thereto, followed by stirring at 160°C for 3 hours. The reaction mixture was allowed to room temperature, neutralized using hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated. Water was added to the residue, the precipitated solid was collected, washed with water, dried in vacuo, so as to obtain the title compound (12mg, 21 percent) as a yellow solid.
21%
Stage #1: With potassium hydroxide In diethylene glycol at 163℃; for 3 h;
Stage #2: With hydrogenchloride In diethylene glycol
A solution prepared by adding (4-bromobenzylydene)-(2,2-diethoxyethyl) amine (synthesized from 4-bromobenzaldehyde, according to the method described in J. Org. Chem., vol. 48, 3344-3346 (1983)) (51.4g, 0.189mmol) to an ice-cold concentrated sulfuric acid (20g) was added to a solution prepared by adding diphosphorus pentoxide (40g) to an ice-cold concentrated sulfuric acid (360g), and the solution was stirred at 160°C for 2 hours. The reaction solution was gradually cooled to 0°C, the solution was filtered through Celite pad, the filtrate was neutralized with sodium carbonate. This solution was further filtrated through Celite pad, this filtrate was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 6-bromoisoquinoline (482mg, 1.2percent) was obtained as an orange oil. Next, to a solution of 6-bromoisoquinoline (382mg, 1.84mmol) in N,N-dimethylformamide (3.8mL) were added zinc cyanide (431mg, 3.67mmol) and tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) under nitrogen atmosphere, and the mixture was stirred at 100°C for 1 hour. Tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) was further added, and the mixture was stirred for 2.5 hours at 100°C. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for extraction, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (hexane : ethyl acetate), and isoquinoline-6-carbonitrile (234mg, 83percent) was obtained as a yellow solid. Lastly, isoquinoline-6-carbonitrile (51mg, 0.331 mmol) was dissolved in diethyleneglycol (1.0mL), potassium hydroxide (9mg, 0.166mmol) was added thereto, followed by stirring at 160°C for 3 hours. The reaction mixture was allowed to room temperature, neutralized using hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated. Water was added to the residue, the precipitated solid was collected, washed with water, dried in vacuo, so as to obtain the title compound (12mg, 21 percent) as a yellow solid.
Reference: [1] Patent: EP1782811, 2007, A1, . Location in patent: Page/Page column 58
[2] Patent: EP1669348, 2006, A1, . Location in patent: Page/Page column 66
[3] Journal of the American Chemical Society, 1939, vol. 61, p. 183
[4] Patent: CN106831575, 2017, A, . Location in patent: Paragraph 0020; 0024
  • 2
  • [ 173089-82-2 ]
  • [ 106778-43-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 17, p. 2583 - 2586
  • 3
  • [ 34784-05-9 ]
  • [ 106778-43-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 17, p. 2583 - 2586
[2] Journal of the American Chemical Society, 1939, vol. 61, p. 183
[3] Patent: CN106831575, 2017, A,
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