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[ CAS No. 5780-66-5 ] {[proInfo.proName]}

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Chemical Structure| 5780-66-5
Chemical Structure| 5780-66-5
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Product Details of [ 5780-66-5 ]

CAS No. :5780-66-5 MDL No. :MFCD02179278
Formula : C5H4N2O Boiling Point : -
Linear Structure Formula :- InChI Key :DXBWJLDFSICTIH-UHFFFAOYSA-N
M.W : 108.10 Pubchem ID :11274980
Synonyms :

Calculated chemistry of [ 5780-66-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 27.42
TPSA : 42.85 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.33
Log Po/w (XLOGP3) : -0.42
Log Po/w (WLOGP) : 0.29
Log Po/w (MLOGP) : -1.48
Log Po/w (SILICOS-IT) : 1.1
Consensus Log Po/w : -0.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.73
Solubility : 19.9 mg/ml ; 0.184 mol/l
Class : Very soluble
Log S (Ali) : -0.02
Solubility : 104.0 mg/ml ; 0.966 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.53
Solubility : 3.15 mg/ml ; 0.0292 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 5780-66-5 ]

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 [ 5780-66-5 ]

* 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 [ 5780-66-5 ]
  • Downstream synthetic route of [ 5780-66-5 ]

[ 5780-66-5 ] Synthesis Path-Upstream   1~13

  • 1
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Reference: [1] Kinetics and Catalysis, 2016, vol. 57, # 5, p. 602 - 609[2] Kinet. Katal., 2016, vol. 57, # 5, p. 607 - 614,8
  • 2
  • [ 109-08-0 ]
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  • [ 31396-35-7 ]
  • [ 98-97-5 ]
  • [ 5780-66-5 ]
  • [ 874-54-4 ]
  • [ 32046-09-6 ]
Reference: [1] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
[2] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
  • 3
  • [ 6164-79-0 ]
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 72℃; for 0.333333 h;
Method 54; Pvrazine-2-carboxaldehyde oxime A IN solution of lithium aluminium hydride in THF (73. 8ml, 73.8mmol) was added to a suspension of methyl pyrazine-2-carboxylate (20g, 145mmol) in anhydrous THF (300. 0ml) at-78°C keeping the reaction temperature below-72°C. On completion of addition the reaction mixture was left to stir at-78°C for a further 20 minutes and then quenched with glacial acetic acid (20. 0ml). The resulting mixture was warmed to room temperature and the volatiles removed by evaporation. The residue was dissolved in 3N hydrochloric acid (116ml) and extracted with DCM. The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution and the solvent evaporated. The residue was purified by chromatography on silica gel eluting with DCM/diethylether (100: 0 then 80: 20 and then 0: 100) to give pyrazine-2-carboxaldehyde (15.67g, 100percent). This was immediately dissolved in chloroform (200ml) cooled to 0°C and hydroxylamine mono-hydrochloride (11. 02g, 159. 5mmol) and triethylamine (24. 2ml, 117. 4mmol) were added. The reaction mixture was then stirred at ambient temperature for 0.5 hour, and the solvent removed by evaporation. The residue suspended in diethylether (500ml) and the insolubles removed by filtration. The filtrate was evaporated and the residue purified by chromatography eluting with DCM/diethylether (100: 0 then 80: 20 and then 0: 100) to give the title compound (5. 5g, 31percent) as a solid. NMR (DMSO-d6) : 8.15 (s, 1H), 8.62 (dd, 2H), 8. 99 (s, 1H).
Reference: [1] Patent: WO2005/40159, 2005, A1, . Location in patent: Page/Page column 212-213
[2] Tetrahedron Letters, 2009, vol. 50, # 28, p. 4030 - 4032
[3] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[4] Chemical Communications, 2007, # 38, p. 3957 - 3959
[5] Journal of the American Chemical Society, 1990, vol. 112, # 17, p. 6248 - 6254
[6] Bulletin des Societes Chimiques Belges, 1982, vol. 91, # 2, p. 153 - 162
[7] Journal of the Chemical Society, Faraday Transactions, 1993, vol. 89, # 1, p. 43 - 48
[8] Bulletin des Societes Chimiques Belges, 1982, vol. 91, # 2, p. 153 - 162
[9] Patent: US2009/306096, 2009, A1, . Location in patent: Page/Page column 19-20
[10] Patent: WO2005/92304, 2005, A2, . Location in patent: Page/Page column 39
[11] Organic Letters, 2012, vol. 14, # 23, p. 6104 - 6107
  • 4
  • [ 6705-33-5 ]
  • [ 5780-66-5 ]
YieldReaction ConditionsOperation in experiment
100 mg With Dess-Martin periodane In dichloromethane at 20℃; for 1 h; To a stirred solution pyrazin-2-ylmethanol (500 mg, 4.545 mmol) in DCM (20 ml) was added Dess-martin periodinane (2.89 g, 6.818 mmol) and stirred for 1 hr at RT. Reaction mass was diluted with DCM (100 ml) washed with saturated sodium bicarbonate solution (50 ml X 2) twice. DCM part was separated, dried over sodium sulfate, evaporated to dryness to get 300 mg crude, which was purified by column chromatography using 100-200 silica and 20percent EtOAc in hexane as eluent to afford pyrazine-2-carbaldehyde (100 mg) as brown liquid.
Reference: [1] Bulletin des Societes Chimiques Belges, 1982, vol. 91, # 2, p. 153 - 162
[2] Molecules, 2009, vol. 14, # 10, p. 4197 - 4212
[3] Patent: WO2014/141110, 2014, A2, . Location in patent: Page/Page column 89; 90
  • 5
  • [ 107-15-3 ]
  • [ 56-81-5 ]
  • [ 290-37-9 ]
  • [ 109-08-0 ]
  • [ 123-32-0 ]
  • [ 5910-89-4 ]
  • [ 6705-33-5 ]
  • [ 108-50-9 ]
  • [ 5780-66-5 ]
Reference: [1] Kinetics and Catalysis, 2016, vol. 57, # 5, p. 602 - 609[2] Kinet. Katal., 2016, vol. 57, # 5, p. 607 - 614,8
  • 6
  • [ 67936-72-5 ]
  • [ 593-56-6 ]
  • [ 5780-66-5 ]
Reference: [1] Patent: US4327213, 1982, A,
  • 7
  • [ 98-97-5 ]
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Reference: [1] Journal of the American Chemical Society, 1990, vol. 112, # 17, p. 6248 - 6254
  • 8
  • [ 107-15-3 ]
  • [ 56-81-5 ]
  • [ 290-37-9 ]
  • [ 109-08-0 ]
  • [ 123-32-0 ]
  • [ 5910-89-4 ]
  • [ 5780-66-5 ]
Reference: [1] Catalysis Communications, 2011, vol. 12, # 12, p. 1067 - 1070
  • 9
  • [ 109-08-0 ]
  • [ 64-19-7 ]
  • [ 73763-94-7 ]
  • [ 5780-66-5 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 38, p. 7259 - 7261
  • 10
  • [ 123-32-0 ]
  • [ 77666-94-5 ]
  • [ 50866-30-3 ]
  • [ 5780-66-5 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 8, p. 915 - 917[2] Khimiya Geterotsiklicheskikh Soedinenii, 1986, # 8, p. 1124 - 1126
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 8, p. 915 - 917[4] Khimiya Geterotsiklicheskikh Soedinenii, 1986, # 8, p. 1124 - 1126
  • 11
  • [ 109-08-0 ]
  • [ 5780-66-5 ]
Reference: [1] Heterocycles, 2003, vol. 60, # 4, p. 953 - 957
  • 12
  • [ 109-08-0 ]
  • [ 25594-37-0 ]
  • [ 31396-35-7 ]
  • [ 98-97-5 ]
  • [ 5780-66-5 ]
  • [ 874-54-4 ]
  • [ 32046-09-6 ]
Reference: [1] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
[2] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
  • 13
  • [ 100-59-4 ]
  • [ 5780-66-5 ]
  • [ 28217-95-0 ]
Reference: [1] Tetrahedron, 2016, vol. 72, # 12, p. 1566 - 1572
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