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[ CAS No. 4964-76-5 ] {[proInfo.proName]}

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Chemical Structure| 4964-76-5
Chemical Structure| 4964-76-5
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Product Details of [ 4964-76-5 ]

CAS No. :4964-76-5 MDL No. :MFCD00870291
Formula : C10H9NO Boiling Point : -
Linear Structure Formula :C6H3(CH3O)C3H3N InChI Key :IVHJSNNMKJWPFW-UHFFFAOYSA-N
M.W : 159.19 Pubchem ID :78666
Synonyms :

Calculated chemistry of [ 4964-76-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.24
TPSA : 22.12 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 2.37
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.214 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.533 mg/ml ; 0.00335 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.82
Solubility : 0.0243 mg/ml ; 0.000153 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 4964-76-5 ]

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 [ 4964-76-5 ]

* 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 [ 4964-76-5 ]
  • Downstream synthetic route of [ 4964-76-5 ]

[ 4964-76-5 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 4964-76-5 ]
  • [ 580-20-1 ]
  • [ 128278-08-0 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 10.2, p. 1890 - 1896[2] Zhurnal Organicheskoi Khimii, 1990, vol. 26, # 10, p. 2191 - 2198
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Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 1562
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  • [ 580-20-1 ]
  • [ 74-88-4 ]
  • [ 4964-76-5 ]
YieldReaction ConditionsOperation in experiment
63%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1 h;
Stage #2: at 20℃; for 1 h;
To a solution of sodium hydride (5.5 g, 137.50 mmol, 60percent) in N,N-dimethylformamide (150 ml) was added quinolin-7-ol (8 g, 55.1 1 mmol). The reaction was stirred for 1 h at 0°C in a water/ice bath. Then CH3I (7.84 g, 55.23 mmol) was added and the solution was stirred for an additional 1 h at room temperature. The reaction was then quenched by the addition of water/ice (700 ml) and extracted with ethyl acetate (3 x 200 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to give a residue, which was purified by a silica gel column with 6 percent ethyl acetate in petroleum ether to afford 7-methoxyquinoline as a red oil (5.5 g, 63percent).LC/MS (ES, m/z): [M+H]+ 160.0'H-NMR (300 MHz, CDC13): δ 8.84 - 8.86 (m, 1H), 8.07 - 8.11 (m, 1H), 7.70 - 7.73 (t, / = 5.1 Hz, 1H), 7.44 (d, / = 2.4 Hz, 1H), 7.20 - 7.30 (m, 2H), 3.95 (s, 3H) Attorney Docket No. BIOE0009-401-PC
25% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 12 h; Inert atmosphere To a solution of quinolin-7-ol (5 g, 34.44 mmol) and Cs2CO3 (22.46 g, 68.89 mmol) in DMF (50 mL) was added iodomethane (2.1 mL, 34.44 mmol). The mixture was stirred at 20 °C for12 b under a nitrogen atmosphere. Water (100 mL) was added and the mixture was extracted with EtOAc (5OmL x 3). The combined organic layers were washed with brine (100 mE x 3), dried over anhydrous Na2SO4 and concentrated in vacuo. The cmde residue was purified by silica gel chromatography (petroleum ether EtOAc = 10: 1) to give the title compound (2.0 g, 25percent) as a yellow oil.
Reference: [1] Synthetic Communications, 2000, vol. 30, # 2, p. 367 - 375
[2] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 82
[3] Patent: WO2016/86200, 2016, A1, . Location in patent: Page/Page column 278
[4] Patent: WO2012/58125, 2012, A1, . Location in patent: Page/Page column 115; 116
  • 4
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YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In ethanol at 20℃; for 24 h; Irradiation In the reactor, 100 mg of substrate 7-methoxy-1,2,3,4-tetrahydroquinoline, 10 mg of boron nitrocarbon photocatalyst, 3 mlOf ethanol and 1.2 equivalents of potassium carbonate, the reaction was stirred at room temperature light illumination 24h, after the reaction was extracted with ethyl acetate, combined with The organic phase was dried, filtered, and the solvent was distilled off under reduced pressure to give a crude product. The column was eluted with petroleum ether: 3: 1 by volume Ethyl acetate mixed solvent, yield 89percent.
Reference: [1] Patent: CN107353245, 2017, A, . Location in patent: Paragraph 0023; 0024
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5487 - 5491[3] Angew. Chem., 2018, vol. 130, # 19, p. 5585 - 5589,5
  • 5
  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
99%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h;
Stage #2: at 20℃; for 1 h;
(a) 7-(Methyloxy)quinoline; A suspension of NaH (3.3g; 137.93mmol) in anhydrous DMF (160ml) was cooled to 0°C with stirring under argon. 7-Quinolinol (8g; 55.17mmol) dissolved in anhydrous DMF (320ml) was added and the mixture was stirred at 0°C under argon for Ih. The mixture was then allowed to warm to rt and MeI (7.8ml; 55.17mmol) was added and the reaction was stirred for Ih. Ice water was then added cautiously and the resulting mixture extracted with EtOAc (3 x 500ml). The organic layer from this extraction was then washed with water (400ml) and brine (400ml). The resulting organic layer was dried with MgSO4 and solvents removed to afford the desired compound (8.76g; 99percent) MS (ES+) m/z 160 (MH+).
Reference: [1] Patent: WO2008/9700, 2008, A1, . Location in patent: Page/Page column 32
  • 6
  • [ 536-90-3 ]
  • [ 56-81-5 ]
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YieldReaction ConditionsOperation in experiment
48% at 120 - 135℃; for 16 h; Sodium nitrobenzene sulfonic acid (3.9 g, 17.3 mmol) and methanesulfonic acid (10 ml) were placed in a 100 ml three-necked flask and stirred. 0.2 g (0.8 mmol) of iron (II) sulfate hydrate, and 3-methoxyaniline (3.09 mL) were added dropwise and the mixture was heated to about 120 ° C.6.3 g of glycerol was added and the reaction was carried out at 135 ° C. for 16 hours. After completion of the reaction, 10Approximately 100 mL of M aqueous NaOH solution was added and extracted with ethyl acetate. The organic layer was collected, dried over anhydrous magnesium sulfate, and the solvent was removed and purified by column chromatography to obtain 4.2 g of RL-0107 (yield: about 48percent).
Reference: [1] Chemical Communications, 2017, vol. 53, # 31, p. 4339 - 4341
[2] Patent: JP2018/118935, 2018, A, . Location in patent: Paragraph 0098
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 42, p. 11124 - 11128[4] Angew. Chem., 2013, vol. 125, # 42, p. 11330 - 11334,5
[5] RSC Advances, 2014, vol. 4, # 41, p. 21456 - 21464
[6] Chemische Berichte, 1924, vol. 57, p. 1246
[7] Journal of the Chemical Society, 1947, p. 437,44
[8] Journal of the Chemical Society, 1934, p. 1419,1421
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Reference: [1] Synlett, 2004, # 3, p. 449 - 452
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  • [ 333383-78-1 ]
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  • [ 6931-19-7 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
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  • [ 6931-19-7 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
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  • [ 536-90-3 ]
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Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
[2] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
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  • [ 93626-91-6 ]
  • [ 637-69-4 ]
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  • [ 14482-11-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1569 - 1572
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  • [ 7022-24-4 ]
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Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
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  • [ 58750-87-1 ]
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Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
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  • [ 4965-36-0 ]
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Reference: [1] Journal of the Chemical Society, 1947, p. 437,44
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  • [ 1963-36-6 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1569 - 1572
  • 16
  • [ 555-03-3 ]
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Reference: [1] Journal of the Chemical Society, 1934, p. 1419,1421
  • 17
  • [ 333383-78-1 ]
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  • [ 6931-19-7 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
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  • [ 333383-79-2 ]
  • [ 4964-76-5 ]
  • [ 6931-19-7 ]
Reference: [1] Heterocycles, 2001, vol. 54, # 1, p. 105 - 108
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  • [ 58196-33-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3415 - 3418
  • 20
  • [ 4964-76-5 ]
  • [ 19500-61-9 ]
YieldReaction ConditionsOperation in experiment
78% With hydrogen In methanol at 20℃; for 16 h; A solution of compound 2-2(12.5 g, 79 mmol) and Pt02 (l . lg, 4.8mmol) in MeOH (500 mL) was stirred at rt for 16 hrs under an atmosphere of H2. The reaction mixture was filtered through Celite.(R).545 and the filtrate was concentrated. The residue was purified by silica gel column chromatography (EtOAc/petroleum ether = 1/8 (v/v)) to give compound 2-3 (9.0 g, 78percent yield) as a yellow oil. LC-MS (ESI): mlz 164 [M+H]+; NMR (500 MHz, CDC13): δ 6.84 (d, J = 8.5 Hz, 1 H), 6.20 (dd, J, = 8.5 Hz, J2 = 2.5 Hz, 1H), 6.04 (d, J = 2.5 Hz, 1H), 3.73 (s, 3H), 3.26 - 3.28 (m, 2H), 2.69 (t, J = 6.5 Hz, 2H), 1.91 (dd, Ji = 6.5 Hz, J2 = 4.5 Hz, 2H) ppm.
73% With hydrogen In methanol at 20℃; To a solution of 7-methoxyquinoline (2.0 g, 12.56 mmol) in methanol (60 ml) was added Pt02 (180 mg, 0.79 mmol). H2 (g) was introduced into above solution and the reaction was stirred overnight at room temperature and then the solids were filtered off. The organics were concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with 3 percent ethyl acetate in petroleum ether to afford 7-methoxy-l,2,3,4-tetrahydroquinoline as a light yellow oil (1.5 g, 73percent).LC/MS (ES, m/z): [M+H]+ 164.0'H-NMR (300 MHz, CD3OD): δ 6.76 (d, / = 8.4 Hz, 1H), 6.09 - 6.17 (m, 2H), 3.69 (s, 1H), 3.19 - 3.23 (m, 2H), 2.64 - 2.69 (t, / = 6.6 Hz, 2H), 1.85 - 1.93 (m, 2H)
38% With platinum(IV) oxide; hydrogen In methanol at 76℃; for 12 h; To a solution of 7-methoxyquinoline (800 mg, 5.03 mmol) in MeOR (8 mL) was added Pt02(137 mg, 0.6 mmol). The mixture was heated to 76 °C for 12 h under a hydrogen atmosphere(15 psi). After cooling the reaction to room temperature, the mixture was concentrated invacuo. The crude residue was purified by silica gel chromatography (petroleum ether EtOAc10: 1) to give the title compound (350 mg, 38percent) as a yellow solid.
Reference: [1] Patent: WO2012/58125, 2012, A1, . Location in patent: Page/Page column 115; 116
[2] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 83
[3] Patent: WO2016/86200, 2016, A1, . Location in patent: Page/Page column 278
[4] Farmaco, Edizione Scientifica, 1954, vol. 9, p. 205,209
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3415 - 3418
[6] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 7956 - 7967
[7] New Journal of Chemistry, 2018, vol. 42, # 20, p. 16694 - 16702
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Reference: [1] Chemical Communications, 2015, vol. 51, # 35, p. 7558 - 7561
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  • [ 36023-06-0 ]
YieldReaction ConditionsOperation in experiment
93.1% With N-Bromosuccinimide In dichloromethane at 20℃; for 12 h; Inert atmosphere 4.2 g of RL-0107 was placed in a 100 mL three-necked flask, and N-bromosuccinimide (NBS) was added thereto. Further, 60 mL of dichloromethane was added, and argon gasReplacement was done. The reaction was further carried out at room temperature for 12 hours. After completion of the reaction, sodium thiosulfate (Na2S 2 O 3) was added and extracted with a water / ethyl acetate system. The organic layer was collected, dried over anhydrous magnesium sulfateAfter drying, the solvent was removed and purified by column chromatography to obtain 5.9 g of RL-0106(Yield: about 93.1percent).
Reference: [1] Chemical Communications, 2017, vol. 53, # 31, p. 4339 - 4341
[2] Patent: JP2018/118935, 2018, A, . Location in patent: Paragraph 0099; 0100
[3] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10413 - 10416
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2358 - 2363
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