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[ CAS No. 17484-36-5 ] {[proInfo.proName]}

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Chemical Structure| 17484-36-5
Chemical Structure| 17484-36-5
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Product Details of [ 17484-36-5 ]

CAS No. :17484-36-5 MDL No. :MFCD00007173
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :JBORNNNGTJSTLC-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :87137
Synonyms :

Calculated chemistry of [ 17484-36-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.72
TPSA : 55.05 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) : -5.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.39
Log Po/w (WLOGP) : 1.91
Log Po/w (MLOGP) : 0.94
Log Po/w (SILICOS-IT) : 0.12
Consensus Log Po/w : 1.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.62
Solubility : 0.401 mg/ml ; 0.0024 mol/l
Class : Soluble
Log S (Ali) : -3.19
Solubility : 0.109 mg/ml ; 0.00065 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.865 mg/ml ; 0.00518 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 17484-36-5 ]

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

Application In Synthesis of [ 17484-36-5 ]

* 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 [ 17484-36-5 ]
  • Downstream synthetic route of [ 17484-36-5 ]

[ 17484-36-5 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 17484-36-5 ]
  • [ 16732-73-3 ]
Reference: [1] Journal of the Chemical Society, 1921, vol. 119, p. 1612[2] Journal of the Chemical Society, 1922, vol. 121, p. 1872
  • 2
  • [ 17484-36-5 ]
  • [ 50868-72-9 ]
YieldReaction ConditionsOperation in experiment
100% With hydrazine hydrate In 1,2-dimethoxyethane for 52 h; Inert atmosphere; Reflux To a solution of 4-methoxy-l -methyls- nitrobenzene (18.0 g, 108 mmol) in 160 mL of DME was added Pd/C (10percent, 0.9 g) under nitrogen. Then hydrazine hydrate (16.17 g, 323 mmol) was added dropwise. The mixture was heated and stirred under reflux for 4h. Then another 3 mL of hydrazine hydrate was <n="72"/>added and stirred under reflux for 2d. Then the reaction mixture was cooled to RT, filtered through celite and evaporated to dryness to give 5-methoxy-2-methylaniline as yellow oil that solidified upon drying under vacuum to give 14.8 g (100percent). 1H NMR (300 MHz, CDCl3): δ 6.94 (d, J = 7.53 Hz, 1H), 6.28 (d, J = 7.53 Hz, I H), 6.26 (s, I H), 3.78 (s, 3H), 3.5 (br, I H), 2.10 (s, 3H), 1.6 (br, 1H).
Reference: [1] Patent: WO2009/117097, 2009, A1, . Location in patent: Page/Page column 70-71
[2] Tetrahedron, 2018, vol. 74, # 12, p. 1294 - 1306
[3] Justus Liebigs Annalen der Chemie, 1882, vol. 215, p. 83
[4] Journal of the Chemical Society, 1929, p. 870
[5] Journal of the Chemical Society, 1925, vol. 127, p. 995
[6] Journal of the Chemical Society, 1929, p. 252
[7] Journal of the American Chemical Society, 1940, vol. 62, p. 1079,1083
[8] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 856 - 865
[9] Journal of Organic Chemistry, 1965, vol. 30, p. 3935 - 3937
[10] Chemistry of Natural Compounds, 1982, vol. 18, # 4, p. 466 - 472[11] Khimiya Prirodnykh Soedinenii, 1982, vol. 18, # 4, p. 498 - 504
[12] Analytical Chemistry, 1992, vol. 64, # 8, p. 837 - 842
[13] Patent: US4426380, 1984, A,
[14] Patent: WO2011/69951, 2011, A1, . Location in patent: Page/Page column 43
[15] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1153 - 1156
  • 3
  • [ 17484-36-5 ]
  • [ 4294-95-5 ]
Reference: [1] Chemische Berichte, 1918, vol. 51, p. 14
  • 4
  • [ 17484-36-5 ]
  • [ 57559-52-1 ]
YieldReaction ConditionsOperation in experiment
59% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 85℃; for 20 h; Intermediate 1 : l-(bromomethvD-4-methoxy-2-nitrobenzene; To a solution of 4-methyl-3-nitroanisole (16.53 mL; 119.64 mmol; leq), in CCU (500 mL) is added N-bromosuccinimide (21.29 g; 119.64 mmol; leq) and azoisobutyronitrile (392.9 mg; 2.39 mmol; 0.02 eq). The mixture is heated at 85°C for 2Oh. The solution is cooled down to room temperature and the precipitate of succinimide is removed by filtration. The filtrate is concentrated to afford a yellow oil. The oil cristallizes after one night at -25°C. It is redissolved in EtOAc (15 mL) and petroleum ether is added. After 2h at -25°C, the compound recrystallizes. After filtration and washing with petroleum ether, the solid is dried under vaccum to afford 17.4 g (59percent) of the title compound as a liquid. 1H NMR (DMSO-dd) δ 7.68 (d, J= 8 Hz, IH), 7.56 (d, J= 3 Hz, IH), 7.33 (dd, J= 8.0, 3.0 Hz, IH), 4.89 (s, 2H), 3.87 (s, 3H). HPLC (max plot) 99percent; Rt 4.09 min.
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[2] Journal of Organic Chemistry, 1984, vol. 49, # 7, p. 1238 - 1246
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 9, p. 3231 - 3244
[4] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 9100 - 9104
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6048 - 6057
[6] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6254 - 6276
[7] Patent: WO2008/101979, 2008, A1, . Location in patent: Page/Page column 52
[8] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 90, p. 12718 - 12721
[9] Patent: US2813128, 1955, ,
[10] Monatshefte fuer Chemie, 1960, vol. 91, p. 1152 - 1161
[11] Polish Journal of Chemistry, 1978, vol. 52, p. 947 - 951
[12] Journal of Heterocyclic Chemistry, 1999, vol. 36, # 1, p. 57 - 64
[13] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 12, p. 3807 - 3815
[14] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3284 - 3291
[15] Patent: US2010/160256, 2010, A1, . Location in patent: Page/Page column 54
[16] Heteroatom Chemistry, 2011, vol. 22, # 3-4, p. 571 - 575
[17] Patent: EP2484668, 2012, A1, . Location in patent: Page/Page column 89; 90
[18] Patent: US2014/57299, 2014, A1, . Location in patent: Page/Page column
[19] Patent: WO2014/31584, 2014, A1, . Location in patent: Page/Page column 49
[20] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 602 - 606
[21] Patent: US9611332, 2017, B2, . Location in patent: Page/Page column 42
[22] Patent: US2004/97575, 2004, A1, . Location in patent: Page 9
[23] Patent: WO2006/103559, 2006, A1, . Location in patent: Page/Page column 67
  • 5
  • [ 2042-14-0 ]
  • [ 74-88-4 ]
  • [ 17484-36-5 ]
Reference: [1] Tetrahedron, 2018, vol. 74, # 12, p. 1294 - 1306
[2] Patent: WO2006/103559, 2006, A1, . Location in patent: Page/Page column 67
  • 6
  • [ 2042-14-0 ]
  • [ 77-78-1 ]
  • [ 17484-36-5 ]
Reference: [1] Synthesis, 1986, # 9, p. 735 - 737
[2] Canadian Journal of Chemistry, 1987, vol. 65, p. 1233 - 1240
[3] Journal of the Chemical Society, 1929, p. 252
[4] Journal of the Chemical Society, 1921, vol. 119, p. 1612[5] Journal of the Chemical Society, 1922, vol. 121, p. 1872
[6] Helvetica Chimica Acta, 1932, vol. 15, p. 394,402
[7] Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1934, vol. 3/2, p. 155,157
[8] Yakugaku Zasshi, 1937, vol. 57, p. 992,995; dtsch. Ref. S. 274, 277[9] Chem.Abstr., 1938, p. 2519
[10] Monatshefte fuer Chemie, 1960, vol. 91, p. 1152 - 1161
[11] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 3091 - 3095[12] Zhurnal Obshchei Khimii, 1960, vol. 30, # 9, p. 3118
  • 7
  • [ 5344-78-5 ]
  • [ 544-97-8 ]
  • [ 17484-36-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 4, p. 817 - 819
  • 8
  • [ 104-93-8 ]
  • [ 119-10-8 ]
  • [ 17484-36-5 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1980, # 11, p. 513 - 514
[2] Journal of the Chemical Society, Chemical Communications, 1980, # 11, p. 513 - 514
  • 9
  • [ 104-93-8 ]
  • [ 108-24-7 ]
  • [ 119-10-8 ]
  • [ 17484-36-5 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1980, # 11, p. 513 - 514
  • 10
  • [ 134-19-0 ]
  • [ 17484-36-5 ]
Reference: [1] Journal of medicinal chemistry, 1966, vol. 9, # 6, p. 828 - 830
  • 11
  • [ 621-02-3 ]
  • [ 17484-36-5 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 252
  • 12
  • [ 106-49-0 ]
  • [ 77-78-1 ]
  • [ 17484-36-5 ]
Reference: [1] Chemische Berichte, 1918, vol. 51, p. 14
  • 13
  • [ 186581-53-3 ]
  • [ 2042-14-0 ]
  • [ 17484-36-5 ]
Reference: [1] Archiv der Pharmazie, 1988, vol. 321, # 5, p. 265 - 272
  • 14
  • [ 67-56-1 ]
  • [ 446-10-6 ]
  • [ 124-41-4 ]
  • [ 17484-36-5 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 4284,4286
  • 15
  • [ 17484-36-5 ]
  • [ 36942-56-0 ]
Reference: [1] Analytical Chemistry, 1992, vol. 64, # 8, p. 837 - 842
  • 16
  • [ 17484-36-5 ]
  • [ 33844-21-2 ]
YieldReaction ConditionsOperation in experiment
80% With hydrogenchloride; potassium permanganate In water Step 1
4-Methoxy-2-nitrotoluene (3.6 g, 18 mmol) and KMnO4 (10 g, 63 mmol) in water (200 mL) were refluxed for 24 h.
The reaction was cooled to ambient temperature and the solids were removed by filtration.
The aqueous phase was made acidic (pH 2) by the addition of 1N HCl and was extracted with CHCl3 (3*50 mL).
The combined organic extracts were dried (MgSO4) and filtered.
The precipitate which formed upon concentration under reduced pressure was collected to give 4-methoxy-2-nitrobenzoic acid (80percent yield).
Reference: [1] Patent: US5665719, 1997, A,
[2] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 8092 - 8103
[3] Chemische Berichte, 1918, vol. 51, p. 14
[4] Patent: US4781750, 1988, A,
  • 17
  • [ 17484-36-5 ]
  • [ 20876-30-6 ]
Reference: [1] Journal of the Chemical Society, 1921, vol. 119, p. 1612[2] Journal of the Chemical Society, 1922, vol. 121, p. 1872
  • 18
  • [ 17484-36-5 ]
  • [ 95-92-1 ]
  • [ 20876-30-6 ]
Reference: [1] Tetrahedron, 1968, vol. 24, p. 6093 - 6109
  • 19
  • [ 17484-36-5 ]
  • [ 20734-74-1 ]
Reference: [1] Patent: WO2011/69951, 2011, A1,
  • 20
  • [ 17484-36-5 ]
  • [ 22996-21-0 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4.5 h; Heating / reflux
Stage #2: With silver (II) carbonate In water; acetone at 20℃;
Example 4Preparation of 3-(7-(l-Methylpiperidin-4-yloxy)quinazolin-2-ylarnino)benzenesulfonanτideStep 1. Preparation of 4-methoxy-2-nitrobenzaldehydeCompound 5 (20.43 g, 0.122 mol, 1.0 eq) was dissolved in 480 ml OfCCl4 under Ar. NBS (48.94 g, 0.275 mol, 2.2 eq) was added to the solution as a solid in one portion followed by addition of benzoyl peroxide (0.67 g, 2.76 mmol). The reaction mixture was stirred under reflux conditions for 4.5 hours. The 1H NMR of an aliquot showed ~ 90percent conversion of starting material to dibromo derivative.The reaction mixture was cooled to RT, and concentrated. CCI4 was chased twice with acetone. The residue was taken into acetone (IL) and Ag2COa (37.1 g, 0.135 mol, 1.1 eq) was added followed by addition of water (100 mL). The reaction mixture was left stirring at RT overnight. TLC ( EtOAc: Hexanes= 3:7) showed a new spot. The reaction mixture was filtered though <n="311"/>PP028218.0002celite, and the filter cake was washed with acetone and the filtrate was concentrated. 340 mL of H2O was added to the crude and the product was extracted with EtOAc (800 mL, 400 mL). The emulsion that formed was filtered through celite and the layers were separated. The organic layer was washed with hrine, dried over Na2SO4, and concentrated to give 8.27 g of crude material, which was purified by column chromatography (EtOAc/Hexanes) giving 14.7 g (67percent yield) of pure compound.
Reference: [1] Patent: WO2007/117607, 2007, A2, . Location in patent: Page/Page column 309-310
[2] Journal of the Chemical Society, 1949, p. Spl. 231
[3] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 856 - 865
[4] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 3091 - 3095[5] Zhurnal Obshchei Khimii, 1960, vol. 30, # 9, p. 3118
[6] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 9100 - 9104
[7] Journal of Organic Chemistry, 1984, vol. 49, # 7, p. 1238 - 1246
[8] Patent: US2813128, 1955, ,
[9] Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 784 - 796
[10] Patent: WO2016/112088, 2016, A1,
[11] Patent: WO2008/101979, 2008, A1,
  • 21
  • [ 17484-36-5 ]
  • [ 105003-90-5 ]
Reference: [1] Patent: US2014/57299, 2014, A1,
[2] Patent: WO2014/31584, 2014, A1,
[3] Patent: US9611332, 2017, B2,
[4] Patent: WO2006/103559, 2006, A1,
  • 22
  • [ 17484-36-5 ]
  • [ 1567360-56-8 ]
Reference: [1] Patent: US2014/57299, 2014, A1,
[2] Patent: WO2014/31584, 2014, A1,
[3] Patent: US9611332, 2017, B2,
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