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[ CAS No. 130345-50-5 ] {[proInfo.proName]}

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Chemical Structure| 130345-50-5
Chemical Structure| 130345-50-5
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Product Details of [ 130345-50-5 ]

CAS No. :130345-50-5 MDL No. :MFCD00805834
Formula : C9H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :UGOIXUFOAODGNI-UHFFFAOYSA-N
M.W : 158.16 Pubchem ID :763958
Synonyms :

Calculated chemistry of [ 130345-50-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.93
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) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.16
Log Po/w (XLOGP3) : 1.04
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 0.23
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 1.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.49 mg/ml ; 0.00941 mol/l
Class : Soluble
Log S (Ali) : -1.53
Solubility : 4.66 mg/ml ; 0.0295 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0861 mg/ml ; 0.000545 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 130345-50-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 130345-50-5 ]

* 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 [ 130345-50-5 ]
  • Downstream synthetic route of [ 130345-50-5 ]

[ 130345-50-5 ] Synthesis Path-Upstream   1~12

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Reference: [1] Acta Pharmacologica Sinica, 2016, vol. 37, # 11, p. 1516 - 1524
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  • [ 258503-93-4 ]
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YieldReaction ConditionsOperation in experiment
73% With lithium tri-butoxyaluminohydride In 1,2-dimethoxyethane at -78℃; for 6.5 h; In a 11 3-neck flask under argon was placed Quinoxaline-6-carbonyl chloride in [600ML] of [

DME. TO THIS SOLUTION WAS ADDED LITHIUM TRI-TERT-BUTOXYALUMINOHYDRIDE (1 EQ. ) AT-78°C] over 1.5 h. The reaction was kept at that temperature for [5H.] Then ice was added, and the reaction was diluted with AcOEt and filtrated over celite. The two layers were separated and the organic phase was washed with [NAHC03] sat. Quinoxaline-6-carbaldehyde was obtained upon evaporating the solvent in 73percent yield as yellowish solid. HPLC : 1.49 min. LC-MS: M/Z ESI: 0.81 min, 159.37 [(M+1). 1H NMR (CDCL3) 6] 10.28 (s, 1H), 8.97 (s, 2H), 8.61 (s, [1H),] 8.27 (q, 6Hz, 9Hz, 2H).
Reference: [1] Patent: WO2004/7491, 2004, A1, . Location in patent: Page 69
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YieldReaction ConditionsOperation in experiment
91% With selenium(IV) oxide In 1,4-dioxane at 200℃; for 3 h; Microwave irradiation b) Quinoxaline-6-carbaldehyde. A suspension of 6-methylquinoxaline (8.0 g; 0.055 mol.) and selenium dioxide (6.77 g; 0.061 mol.) in 1,4-dioxane (5.0 mL) was irradiated at 200° C. for 30 min. in a Biotage Initiator microwave synthesizer. The above procedure was repeated five further times and the combined, cooled reaction mixtures were dissolved in CH2Cl2, filtered through a plug of celite, and concentrated in vacuo. Purification via flash column chromatography (silica gel, 20-50percent ethyl acetate in hexanes) followed by crystallization from CH2Cl2 provided quinoxaline-6-carbaldehyde (40.0 g, 91percent) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.25 (s, 1H) 8.95 (s, 2H) 8.57 (d, J=1.3 Hz, 1H) 8.24 (dd, J=8.6, 1.5 Hz, 1H) 8.20 (d, J=8.6 Hz, 1H). MS(ES+) m/e 159 [M+H]+.
91% With selenium(IV) oxide In 1,4-dioxane at 220℃; for 3 h; Microwave heating A suspension of 3,4-diaminotoluene (50.0 g; 0.409 mol.) and glyoxal (40percent aq. soln.; 52.0 mL; 0.450 mol.) in water (150 mL) and CH3CN (20.0 mL) was heated to 60 0C for 1 h. Heating was then discontinued and brine (100 mL) was added. The solution was extracted with EtOAc (3 x 150 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification via distillation under reduced pressure (1200C, 10 torr) provided 6-methylquinoxaline (48.0 g, 81 percent) as a clear, colorless oil. 1 H NMR (400 MHz, CDCl3) δ ppm 2.61 (s, 3 H) 7.61 (dd, J=8.59, 1.77 Hz, 1 H) 7.88 (s, 1 H) 8.00 (d, J=8.59 Hz, 1 H) 8.79 (dd, J=9.85, 1.77 Hz, 2 H) MS(ES+) m/e 145 [M+H]+. A suspension of 6-methylquinoxaline (8.O g; 0.055 mol.) and selenium dioxide (6.77 g; 0.061 mol.) in 1 ,4-dioxane (5.0 mL) was irradiated at 2000C for 30 min. in a Biotage Initiator microwave synthesizer. The above procedure was repeated five further times and the combined, cooled reaction mixtures were dissolved in CH2CI2, filtered through a plug of celite, and concentrated in vacuo. Purification via flash column chromatography (silica gel,20-50percent ethyl acetate in hexanes) followed by crystallization from CH2CI2 provided quinoxaline-6-carbaldehyde (40.0 g, 91percent) as a white solid. 1H NMR EPO <DP n="114"/>(400 MHz, CDCI3) δ ppm 10.25 (s, 1 H) 8.95 (s, 2 H) 8.57 (d, J=1.3 Hz, 1 H) 8.24 (dd, J=8.6, 1.5 Hz, 1 H) 8.20 (d, J=8.6 Hz, 1 H). MS(ES+) m/e 159 [M+H]+.
91% With selenium(IV) oxide In 1,4-dioxane at 200℃; for 0.5 h; Microwave irradiation A suspension of 6-methylquinoxaline (8.0 g; 0.055 mol.) and selenium dioxide (6.77 g; 0.061 mol.) in 1 ,4-dioxane (5.0 mL) was irradiated at 200 0C for 30 min. in a Biotage Initiator microwave synthesizer. The above procedure was repeated five further times and the combined, cooled reaction mixtures were dissolved in CH2CI2, filtered through a plug of celite, and concentrated in vacuo. Purification via flash column chromatography (silica gel, 20-50percent ethyl acetate in hexanes) followed by crystallization from CH2CI2 provided quinoxaline-6-carbaldehyde (40.0 g, 91 percent) as a white solid. 1H NMR (400 MHz, CDCI3) δ ppm 10.25 (s, 1 H) 8.95 (s, 2 H) 8.57 (d, J=1.3 Hz, 1 H) 8.24 (dd, J=8.6, 1.5 Hz, 1 H) 8.20 (d, J=8.6 Hz, 1 H). MS(ES+) m/e 159 [M+H]+.
64% With selenium(IV) oxide In ethyl acetate at 160℃; for 7 h; Example 242 : Synthesis of (1E,6E)-1-(4-hydroxyphenyl)-7-(quinoxalin-6-yl)hepta-1,6-diene-3,5-dione (CU348); (1) Synthesis of quinoxaline-6-carboxaldehyde; 6-Methylquinoxaline (500 mg, 3.47 mmol) and selenium dioxide (423 mg, 3.81 mmol) in a sealed vessel were stirred at 160°C for 7 h. After cooled to room temperature, the reaction mixture was dissolved in ethyl acetate. The solution was washed with brine twice, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 80/20 to 60/40) to obtain the title compound as a pale brown solid (355 mg, 64percent).
10% at 160℃; for 72 h; 6-Methylquinaxoline (100 g, 0.69 mol) was heated in a sealed tube to 160 0C and was then added selenium dioxide (100 g, 0.90 mol). The sealed tube was then stirred at 160 0C for 3 days, then allowed to cool to room temperature. The contents solidified and were dissolved in dichloromethane. Solids were filtered through a celite/silica gel cake. The cake was washed with dichloromethane and washes were combined and concentrated to give a pinkish solid, which was washed with hexane and then dried under vacuum to give quinoxaline-6- carbaldehyde as a white solid (50.5 g, contained ca. 10percent of 6-methylquinaxoline).

Reference: [1] Patent: US2007/179144, 2007, A1, . Location in patent: Page/Page column 4
[2] Patent: WO2006/127458, 2006, A2, . Location in patent: Page/Page column 112-113
[3] Patent: WO2006/133381, 2006, A2, . Location in patent: Page/Page column 7
[4] Patent: EP2123637, 2009, A1, . Location in patent: Page/Page column 66
[5] Patent: WO2006/26305, 2006, A1, . Location in patent: Page/Page column 33
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YieldReaction ConditionsOperation in experiment
68% With sodium periodate In 1,4-dioxane; water; <i>tert</i>-butyl alcohol for 3 h; Quinoxaline-6-carbaldehyde: To a mixture of 6-Vinyl-quinoxaline (0.68 g, 4.35 mmol) in dioxane (44 mL) and water (35 mL) was added osmium tetraoxide (2.5percent wt in t-BuOH, 2.18 mL, 0.17 mmol) followed by sodium periodate (2.79 g, 13.1 mmol) and the reaction stirred for 3 h. The solution was diluted with ethyl acetate (150 mL) and then washed with water (3.x.75 mL) followed by brine (75 mL). The organics were dried with magnesium sulfate, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel using 10-20percent ethyl acetate in dichloromethane as eluant yielded 470 mg (68percent yield) of Quinoxaline-6-carbaldehyde as a white solid. 1H NMR (DMSO-d6): 10.30 (s,1H), 9.11 (d,2H,J=1.9 Hz), 8.74 (d,1H,J=1.4 Hz), 8.26 (m,2H). LC/MS (Method A): r.t.=0.69 min., purity=94.8percent, calculated mass=158, [M+H]+=159.
Reference: [1] Patent: US2006/270848, 2006, A1, . Location in patent: Page/Page column 37
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  • [ 50998-17-9 ]
  • [ 201230-82-2 ]
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Reference: [1] Tetrahedron, 2007, vol. 63, # 27, p. 6252 - 6258
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  • [ 875558-38-6 ]
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YieldReaction ConditionsOperation in experiment
93.7% With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 0.5 h; [0185] To a solution of N-methoxy-N-methylquinoxaline-6-carboxamide (4.34 g, 20 mmol, 1.0 eq.) in THF (40 mL) cooled at -78 °C was added DiBAl-H (40 mL, 40 mmol, 2.0 eq.) dropwise. The resulted mixture was stirred at -78 °C for 30 min, then quenched by the addition of aqueous NH4C1 solution. The mixture was adjusted to pH 7 with HCl (IN, 60 mL) and extracted with EA (50 mL X 3). The organic layers were combined, dried over anhydrous Na2S04 and concentrated. The resulting residue was purified via flash column chromatography (PE/EA=4/l,v/v) to afford quinoxaline-6- carbaldehyde
93.7% With diisobutylaluminium hydride In tetrahydrofuran at -78℃; for 0.5 h; To a solution of N-methoxy-N-methylquinoxaline-6-carboxamide (4.34 g, 20 mmol, 1.0 eq.) in THF (40 mL) cooled at -78 °C was added DiBAl-H (40 mL, 40 mmol, 2.0 eq.) dropwise. The resulted mixture was stirred at -78 °C for 30 min, then quenched by the addition of aqueous NH4C1 solution. The mixture was adjusted to pH 7 with HC1 (1 N, 60 mL) and extracted with EA (50 mL X 3). The organic layers were combined, dried over anhydrous Na2S04 and concentrated. The resulting residue was purified via flash column chromatography (PE/EA=4/l,v/v) to afford quinoxaline-6- carbaldehyde as yellow solid (2.96 g, 93.7percent)
82% With diisobutylaluminium hydride In tetrahydrofuran; toluene at -10℃; Stage 3 A solution of Compound (vi) in THF is treated with a solution of DIBAL-H in toluene at approximately -10° C. The mixture is quenched into aqueous hydrochloric acid and warmed to 20° C. The mixture is diluted with brine. The aqueous phase is removed and backextracted with ethyl acetate. The combined organics are washed with brine, partially concentrated, diluted with heptane, partially distilled again, diluted with heptane, cooled, and filtered. The resulting Compound (vii) wetcake is washed with heptane and dried under vacuum at 50° C.
Reference: [1] Patent: WO2013/43935, 2013, A1, . Location in patent: Paragraph 0185
[2] Patent: WO2013/40515, 2013, A1, . Location in patent: Paragraph 0196
[3] Patent: US2007/179144, 2007, A1, . Location in patent: Page/Page column 5; 6
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Reference: [1] Patent: US6559308, 2003, B1,
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Reference: [1] Patent: US5028606, 1991, A,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3771 - 3774
[2] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 255 - 264
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3771 - 3774
[2] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 255 - 264
[3] Patent: WO2013/40515, 2013, A1,
[4] Patent: WO2013/43935, 2013, A1,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3771 - 3774
[2] European Journal of Medicinal Chemistry, 2012, vol. 48, p. 255 - 264
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Reference: [1] Patent: WO2006/127458, 2006, A2,
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