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[ CAS No. 127406-08-0 ] {[proInfo.proName]}

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Chemical Structure| 127406-08-0
Chemical Structure| 127406-08-0
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Product Details of [ 127406-08-0 ]

CAS No. :127406-08-0 MDL No. :MFCD02684109
Formula : C11H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :QEJFDPPZUXABRM-UHFFFAOYSA-N
M.W : 184.19 Pubchem ID :3853519
Synonyms :

Calculated chemistry of [ 127406-08-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.86
TPSA : 42.85 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.96
Log Po/w (MLOGP) : 0.24
Log Po/w (SILICOS-IT) : 2.63
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.57
Solubility : 0.491 mg/ml ; 0.00267 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 1.04 mg/ml ; 0.00567 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.12
Solubility : 0.014 mg/ml ; 0.0000762 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 127406-08-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 127406-08-0 ]

* 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 [ 127406-08-0 ]
  • Downstream synthetic route of [ 127406-08-0 ]

[ 127406-08-0 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 14508-49-7 ]
  • [ 59016-93-2 ]
  • [ 127406-08-0 ]
YieldReaction ConditionsOperation in experiment
90% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
90% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
90% With C46H49BrClFeN3Pd; copper diacetate; caesium carbonate In 1,4-dioxane at 110℃; for 24 h; General procedure: A 10 mL round-bottom flask was charged with the prescribedamount of catalyst Pd/Cu, aryl chlorides (0.5 mmol), phenylboronicacids containing hydroxymethyl (0.75 mmol), Cs2CO3 (1.0 mmol)and dioxane (5 mL) in air. The reaction mixture was then placedin an oil bath and heated at 110 C for 24 h. After removal of thesolvent, the resulting residue was purified by flash chromatographyon silica gel using CH2Cl2 as eluent. The products 4a–k, and4m are known compounds [6,9] except for 4l and 4n.
Reference: [1] Inorganica Chimica Acta, 2014, vol. 423, # PART A, p. 11 - 15
[2] Inorganica Chimica Acta, 2014, vol. 423, # 1, p. 11 - 15
[3] Inorganica Chimica Acta, 2014, # PA, p. 11 - 15
  • 2
  • [ 14508-49-7 ]
  • [ 87199-17-5 ]
  • [ 127406-08-0 ]
YieldReaction ConditionsOperation in experiment
97% With sodium carbonate In ethanol; toluene for 18 h; Heating / reflux Step A
Ethanol (13 ml) and 1.0M Na2CO3 (27.5 ml) were added to a suspension of 2-chloropyrazine (4.0 g, 34.6 mmole), 4-formylphenylboronic acid (6.8 g, 45.0 mmole), and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.7 mmole) in toluene (55 ml).
The mixture was refluxed for 18 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated.
Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 6.2 g (97percent) of 4-(2-pyrazinyl)benzaldehyde.
42%
Stage #1: With sodium carbonate In ethanol; water; toluene for 18 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In ethanol; water; ethyl acetate; toluene
[0410] Step A: [0411] 1M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 2-chloropyrazine (2.30 g, 20.06 mmol), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.56 g (42percent) of 4-pyrazinylbenzaldehyde.
Reference: [1] Patent: US2005/250713, 2005, A1, . Location in patent: Page/Page column 29-30
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 35, p. 6944 - 6952
[3] Patent: US2004/18994, 2004, A1, . Location in patent: Page/Page column 61
  • 3
  • [ 4009-98-7 ]
  • [ 127406-08-0 ]
YieldReaction ConditionsOperation in experiment
71% With sodium hexamethyldisilazane In tetrahydrofuran Step A
2-[4-[(E)-2-methoxyethenyl]phenyl]-pyrazine
Sodium hexamethyldisilazide (10.80 mL, 10.80 mmol, 11.0M in THF) was added to a suspension of methoxymethyltriphenylphosphonium chloride (3.72 g, 10.80 mmol) in THF (20 mL) at -10° C., and the red-orange mixture was stirred for 15 min at -10° C. A solution of 4-pyrazinylbenzaldehyde (1.00 g, 5.43 mmol) prepared as described in reference example 17) in THF (3 mL) was added dropwise, and stirring was continued at -10° C. for 1 h.
The reaction mixture was quenched with sat.
aq. NH4Cl, extracted with ethyl acetate, the organic layer dried with Na2SO4, and concentrated in vacuo.
Purification by medium pressure liquid chromatography (SiO2, 3:1 hexane/ethyl acetate) yielded 820 mg (71percent) of the title compound (E:Z=1:1). MS 213 (M+H)+.
Reference: [1] Patent: US2003/220272, 2003, A1,
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