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[ CAS No. 1084334-86-0 ] {[proInfo.proName]}

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Chemical Structure| 1084334-86-0
Chemical Structure| 1084334-86-0
Structure of 1084334-86-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1084334-86-0 ]

CAS No. :1084334-86-0 MDL No. :MFCD28144504
Formula : C24H20BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UUOYDHJVGOATFJ-UHFFFAOYSA-N
M.W : 365.23 Pubchem ID :57746617
Synonyms :

Calculated chemistry of [ 1084334-86-0 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 116.39
TPSA : 43.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 5.69
Log Po/w (WLOGP) : 4.5
Log Po/w (MLOGP) : 4.2
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 3.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.99
Solubility : 0.000371 mg/ml ; 0.00000102 mol/l
Class : Moderately soluble
Log S (Ali) : -6.37
Solubility : 0.000155 mg/ml ; 0.000000423 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.12
Solubility : 0.00000274 mg/ml ; 0.0000000075 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.82

Safety of [ 1084334-86-0 ]

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 [ 1084334-86-0 ]

* 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 [ 1084334-86-0 ]
  • Downstream synthetic route of [ 1084334-86-0 ]

[ 1084334-86-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 503299-24-9 ]
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YieldReaction ConditionsOperation in experiment
73%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at 20℃; for 4 h;
2-2. Preparation of compound 10[173]N-(4-bromophenyl)-N-phenyl-[1,1’-biphenyl]-4-amine (15.0 g, 37.5 mmol) was dissolved in tetrahydrofurane (190.0 mL) and n-butyl lithium (2.5 M in hexane) (22.0 mL) was added to the mixture at -78 . The mixture was stirred for 1 hour and trimethoxyborane (6.3 mL, 56.21 mmol) was added thereto. After stirring the whole mixture for 4 hours at room temperature, the mixture was extracted with ethyl acetate (200.0 mL) and the obtained organic layer was washed with distilled water (100.0 mL). The organic solvent was removed under the reduced pressure. The obtained solid was washed with hexane, filtered and dried to obtain (4-([1,1-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (10.0 g, 73percent).
61%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 25 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; for 1 h;
(iii)
Synthesis of 4-[N-(biphenyl-4-yl)-N-phenylamino]phenylboronic acid
A synthesis scheme (C-4) of 4-[N-(biphenyl-4-yl)-N-phenylamino]phenylboronic acid is shown below.
In a 300-mL three-neck flask, 7.0 g (18 mmol) of 4-bromo-4'-phenyltriphenylamine was put, and the atmosphere in the flask was substituted by nitrogen.
Then, 80 mL of tetrahydrofuran (abbreviation: THF) was added thereto, and the mixture was stirred at -78° C. for 10 minutes.
After that, 13 mL (21 mmol) of an n-butyllithium hexane solution (1.63 mol/L) was dropped into this solution from a syringe, and the solution was stirred at -78° C. for 1 hour.
After a certain time, 3.5 mL of trimethyl borate was added to the reaction mixture and the mixture was stirred at -78° C. for 1 hour, then stirred for 24 hours while changing the temperature from -78° C. to room temperature.
After stirring, 100 mL of 1M dilute hydrochloric acid was added to the solution, and the mixture was stirred at room temperature for 1 hour.
After stirring, ethyl acetate was added to this solution for extraction.
After extraction, the extract was washed with a saturated saline.
After washing, magnesium sulfate was added to the extract for drying.
After the drying, magnesium sulfate was removed by suction filtration to give a filtrate.
The obtained filtrate was concentrated and recrystallized from a mixed solvent of chloroform and hexane to give 4.0 g of the target substance, 4-[N-(biphenyl-4-yl)-N-phenylamino]phenylboronic acid in a yield of 61percent.
Reference: [1] Patent: WO2014/104704, 2014, A1, . Location in patent: Paragraph 172-173
[2] Patent: US2013/76237, 2013, A1, . Location in patent: Paragraph 0200; 0201
  • 2
  • [ 121-43-7 ]
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YieldReaction ConditionsOperation in experiment
56%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at -78 - 20℃; for 25 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; for 1 h;
Step 1: Synthesis of 4-[λT-(biphenyl-4-yl)-λT-phenyl]aminophenylboronic acid][0410]A synthetic scheme of 4-[N-(biphenyl-4-yl)-λT-phenyl]aminophenylboronic acid in Step 1 is shown in the following (η-l). [0411] <n="176"/>[0412]In a 300-mL three-neck flask, 7.0 g (18 mmol) of 4-bromo-4'-phenyltriphenylamine was put, and the atmosphere in the flask was substituted by nitrogen. Then, 80 mL of tetrahydrofuran (abbreviation: THF) was added thereto, and the mixture was stirred at -780C for 10 minutes. After that, 13 mL (21 mmol) of an n-butyllithium hexane solution (1.63 mol/L) was dropped onto this solution from a syringe, and the solution was stirred at -780C for 1 hour. After the stirring, 3.5 mL (31 mmol) of trimethyl borate was added to the reaction mixture, and the mixture was stirred at -78 0C for 1 hour and at room temperature for 24 hours. After the reaction, 100 mL of IM dilute hydrochloric acid was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. After the stirring, this solution was extracted with ethyl acetate, and an organic layer was washed with a saturated saline solution. After the washing, magnesium sulfate was added to the organic layer, and the organic layer was dried. After the drying, magnesium sulfate was removed by suction filtration to obtain filtrate. The obtained filtrate was concentrated and recrystallized with a mixture solvent of chloroform and hexane to obtain 3.6 g of an object at a yield of 56 percent.
Reference: [1] Patent: WO2009/72587, 2009, A1, . Location in patent: Page/Page column 174-175
  • 3
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Reference: [1] Patent: US2013/76237, 2013, A1,
  • 4
  • [ 4432-94-4 ]
  • [ 1084334-86-0 ]
Reference: [1] Patent: US2013/76237, 2013, A1,
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  • [ 122-39-4 ]
  • [ 1084334-86-0 ]
Reference: [1] Patent: US2013/76237, 2013, A1,
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  • [ 32228-99-2 ]
  • [ 1084334-86-0 ]
Reference: [1] Patent: WO2014/104704, 2014, A1,
  • 7
  • [ 589-87-7 ]
  • [ 1084334-86-0 ]
Reference: [1] Patent: WO2014/104704, 2014, A1,
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