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[ CAS No. 70500-72-0 ] {[proInfo.proName]}

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Product Details of [ 70500-72-0 ]

CAS No. :70500-72-0 MDL No. :MFCD04117979
Formula : C9H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DBSPUDKBNOZFMX-UHFFFAOYSA-N
M.W : 161.16 Pubchem ID :10975787
Synonyms :

Calculated chemistry of [ 70500-72-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.79
TPSA : 53.35 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) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 1.65
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 1.48
Consensus Log Po/w : 1.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.408 mg/ml ; 0.00253 mol/l
Class : Soluble
Log S (Ali) : -2.55
Solubility : 0.454 mg/ml ; 0.00282 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.466 mg/ml ; 0.00289 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 70500-72-0 ]

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 [ 70500-72-0 ]

* 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 [ 70500-72-0 ]
  • Downstream synthetic route of [ 70500-72-0 ]

[ 70500-72-0 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 70500-72-0 ]
  • [ 49609-15-6 ]
Reference: [1] Patent: WO2017/32840, 2017, A1,
  • 2
  • [ 127033-74-3 ]
  • [ 70500-72-0 ]
YieldReaction ConditionsOperation in experiment
54% With aluminum (III) chloride In chlorobenzene at 120℃; Cooling with ice To a suspension of compound 3 (1 g, 3.95 mmol) in chlorobenzene (30 mL) was added portionwise aluminum trichloride (3.16 g, 23.69 mmoL) under ice bath.The reaction system was gradually heated to 120 ° C, refluxed for 3-5 h, and the reaction system was monitored by TLC.After the completion of the reaction, the reaction system was evaporated to dryness under reduced pressure and purified by silica gel column chromatography.Compound 4 was obtained in 54percent yield.Suggest an edit
Reference: [1] Synthesis, 1997, # 1, p. 87 - 90
[2] Tetrahedron Letters, 1999, vol. 40, # 24, p. 4505 - 4506
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5561 - 5578
[4] Patent: CN108101926, 2018, A, . Location in patent: Paragraph 0033; 0034; 0035
[5] Patent: WO2008/24481, 2008, A2, . Location in patent: Page/Page column 32
[6] Patent: CN107098855, 2017, A, . Location in patent: Paragraph 0036; 0038
  • 3
  • [ 15116-41-3 ]
  • [ 70500-72-0 ]
YieldReaction ConditionsOperation in experiment
53% With aluminum (III) chloride In chlorobenzene at 0 - 120℃; Intermediate 14:[0130] AICI3 (11.5 g, 86.3 mmol) was added portion-wise to a suspension of intermediate 13 (4.2 g, 16.6 mmol) in chlorobenzene (90 mL) at 0°C. The reaction mixture was gradually warmed to 120°C and stirred for 3 h. The mixture was poured into ice water and the resulting precipitate was collected by filtration, washed with water, and purified by flash chromatography on silica gel column (elution with DCM/MeOH = 60:1) to give 7-hydroxyquinolin-2(lH)-one (intermediate 14) (1.41 g, 53percent) as a white solid.
43% at 120 - 180℃; for 2.08333 h; [00220] N-(3-methoxyphenyl)cinnamamide (18 g, 71 mmol ) was added AICI3 (28.4 g, 213 mmol) and the mixture heated at 180 °C for 5 min. and then at 120 °C for 2 h. The mixture was then poured into ice and the resulting precipitate was collected by filtration, washed with water, and purified by flash chromatography eluting withdichloromethane:methanol (60: 1) to give the title compound as a white solid, (5 g, 43percent), MS (ESI): m/z 162 [M + H]+.
Reference: [1] Patent: WO2012/3418, 2012, A2, . Location in patent: Page/Page column 50
[2] Patent: WO2014/85284, 2014, A1, . Location in patent: Paragraph 00220
[3] Patent: WO2017/115287, 2017, A1, . Location in patent: Page/Page column 19
  • 4
  • [ 22246-18-0 ]
  • [ 70500-72-0 ]
YieldReaction ConditionsOperation in experiment
89% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 66℃; for 4 h; Into a 1000mL reaction flask put 100g of 3, 4-dihydro-7-hydroxyl-2-quinolinone, and add 500mL of tetrahydrofuran, and then add 140g of DDQ, after that heated at 66 ° C, stirred and refluxed for 4 hours, after the reaction is complete, add 1mol / L sodium thiosulfate 500mL aqueous solution, and then filtered and dried, and then obtained 7-hydroxyl-2-quinolinone as an off-white powder 88g, yield 89percent, purity 99.7percent.
75%
Stage #1: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20 - 50℃; for 2 h; Inert atmosphere
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1 h; Inert atmosphere
To a solution of compound 4 (25 g, 0.153 mol, 1.0 eq) in THF (125 mL) at room temperature under a nitrogen atmosphere and stirred for 10-15 min, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) added portion wise (37.16 g, 0.163, 1.07 eq) to the reaction mixture. Stirred the reaction at 45-50 °C for 2 h. The progress of the reaction monitored by TLC, reaction mixture was cooled to 25-30 °C, added NaHCO3 (27.5 g, 0.327, 2.14 eq) and water (250 mL) to the reaction mixture, stirred for 1 h at room temperature, solid filtered and washed with water (50 mL). Wet cake was triturated with Isopropyl alcohol (75 mL), filtered and washed with isopropyl alcohol (25 mL) to obtain pure compound 1 (18.5 g, 0.114 mol, 75 percent) as an off-white solid, m.p. 233-235 °C. 1H NMR (400 MHz, DMSO-d6)δ (ppm) 11.47 (br s, 1H), 10.07 (s, 1H), 7.73 (d, J) 9.44 Hz, 1H), 7.43 (d, J) 8.52 Hz, 1H) 6.67 (s, 1H) 6.61 (d, J) 6.48 Hz, 1H), 6.20 (d, J) 9.4 Hz, 1H); 13C NMR (100 MHz, DMSO-d6)δ (ppm) 162.3, 159.5, 140.7, 140.0, 129.2, 117.4, 112.3, 111.5, 99.8; C9H7NO2 [M-1] calcd. 160.1.
20.3 g With 2,3-dichloro-5,6-dicyanohydroquinone In tetrahydrofuran at 0 - 30℃; for 11 h; A solution of 4,5-dichloro-3,6-dihydroxyphthalonitrile (40.86 gm) in tetrahydrofuran (100 ml) was added to a pre-cooled mixture of 7-hydroxy-3,4-dihydroquinolin-2(1H)-one (25 gm) and tetrahydrofuran (50 ml) at 0-5°C and stirred the reaction mixture for 20 min at the same temperature. Raised the temperature of the reaction mixture to 25-30°C and stirred for 1 1 hrs at the same temperature. Filtered the solid, washed with tetrahydrofuran and suck dried the material. Methanol (125 ml) was added to the obtained compound at 25-30°C. Heated the reaction mixture to 50-55°C and stirred for 1 hr at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 1 hr at the same temperature. Filtered the solid, washed with methanol and dried the material to get the title compound. (0289) Yield: 20.3 gm.
Reference: [1] Patent: CN107098855, 2017, A, . Location in patent: Paragraph 0022-0035
[2] Asian Journal of Chemistry, 2018, vol. 30, # 4, p. 834 - 836
[3] Patent: WO2018/87775, 2018, A1, . Location in patent: Page/Page column 33
  • 5
  • [ 591-27-5 ]
  • [ 70500-72-0 ]
Reference: [1] Patent: US5410054, 1995, A,
[2] Asian Journal of Chemistry, 2018, vol. 30, # 4, p. 834 - 836
  • 6
  • [ 220364-99-8 ]
  • [ 70500-72-0 ]
Reference: [1] Heterocycles, 1999, vol. 50, # 1, p. 453 - 462
  • 7
  • [ 536-90-3 ]
  • [ 70500-72-0 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 24, p. 4505 - 4506
[2] Patent: WO2012/3418, 2012, A2,
[3] Patent: WO2014/85284, 2014, A1,
[4] Patent: CN108101926, 2018, A,
  • 8
  • [ 93-35-6 ]
  • [ 70500-72-0 ]
Reference: [1] Journal of the Chinese Chemical Society, 2000, vol. 47, # 2, p. 389 - 395
  • 9
  • [ 93499-67-3 ]
  • [ 70500-72-0 ]
Reference: [1] Heterocycles, 1999, vol. 50, # 1, p. 453 - 462
  • 10
  • [ 50297-40-0 ]
  • [ 70500-72-0 ]
Reference: [1] Asian Journal of Chemistry, 2018, vol. 30, # 4, p. 834 - 836
  • 11
  • [ 14737-89-4 ]
  • [ 70500-72-0 ]
Reference: [1] Patent: CN107602462, 2018, A,
  • 12
  • [ 39856-08-1 ]
  • [ 70500-72-0 ]
Reference: [1] Patent: CN107602462, 2018, A,
  • 13
  • [ 20329-98-0 ]
  • [ 70500-72-0 ]
Reference: [1] Patent: CN107602462, 2018, A,
  • 14
  • [ 10263-19-1 ]
  • [ 70500-72-0 ]
Reference: [1] Patent: CN107602462, 2018, A,
  • 15
  • [ 110-52-1 ]
  • [ 70500-72-0 ]
  • [ 203395-59-9 ]
YieldReaction ConditionsOperation in experiment
41% With potassium carbonate In ethanolReflux Intermediate 14:[0130] AICI3 (11.5 g, 86.3 mmol) was added portion-wise to a suspension of intermediate 13 (4.2 g, 16.6 mmol) in chlorobenzene (90 mL) at 0°C. The reaction mixture was gradually warmed to 120°C and stirred for 3 h. The mixture was poured into ice water and the resulting precipitate was collected by filtration, washed with water, and purified by flash chromatography on silica gel column (elution with DCM/MeOH = 60:1) to give 7-hydroxyquinolin-2(lH)-one (intermediate 14) (1.41 g, 53percent) as a white solid. Intermediate 15:
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 11, p. 1471 - 1480
[2] Patent: WO2012/3418, 2012, A2, . Location in patent: Page/Page column 51
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 658 - 667
[4] Patent: WO2008/24481, 2008, A2, . Location in patent: Page/Page column 42
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7141 - 7153
  • 16
  • [ 70500-72-0 ]
  • [ 129722-25-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 658 - 667
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7141 - 7153
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