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[ CAS No. 369-26-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 369-26-6
Chemical Structure| 369-26-6
Chemical Structure| 369-26-6
Structure of 369-26-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 369-26-6 ]

CAS No. :369-26-6 MDL No. :MFCD08689743
Formula : C8H8FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ABELEDYNIKPYTP-UHFFFAOYSA-N
M.W :169.15 Pubchem ID :12541234
Synonyms :

Calculated chemistry of [ 369-26-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.08
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 1.4
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.01 mg/ml ; 0.00598 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.593 mg/ml ; 0.0035 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.692 mg/ml ; 0.00409 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 369-26-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 369-26-6 ]

* 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 [ 369-26-6 ]
  • Downstream synthetic route of [ 369-26-6 ]

[ 369-26-6 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 329-59-9 ]
  • [ 369-26-6 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethyl acetate at 20℃; Step B: Methyl 3-amino-4-fluorobenzoate; To a solution of methyl 4-fluoro-3-nitrobenzoate (6.57 g, 33 mmol) in EtOAc (75 mL) was added 10percent palladium on carbon (0.66 g). The suspension was transferred to a Fisher-Porter flask and installed in a hydrogenation apparatus. The flask was charged with H2 (25 psi) and stirred overnight at rt. The palladium was removed by filtration through a Celite plug, and the product was concentrated to generate a yellow oil, which darkened upon standing, in quantitative yield (5.51 g, 33 mmol). MS (ESI) m/z = 170 [M+H]+.
68% With hydrogenchloride; iron In methanol; water for 48 h; Reflux; Inert atmosphere To a stirring solution of 4-fluoro-3-nitrobenzoic acid (25 g, 126 mmol) in MeOH (20 mL) was added Fe (28 g, 502 mmol), followed by addition of con. HCl (5 mL). The mixture was heated to reflux for two days, cooled to room temperature, and then filtered. The filtrate was concentrated in vacuo to give the desired product as a solid (15 g, 68percent). LC-MS (ES) m/z = 170.1 (M+H)+ 1H NMR (400 MHz, MeOD) δ ppm 7.39 (m, 2 H), 6.94 (m, 1 H), 3.91 (br, 5 H).
Reference: [1] Patent: WO2009/76140, 2009, A1, . Location in patent: Page/Page column 186
[2] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044
[3] Synlett, 2010, # 20, p. 3019 - 3022
[4] Patent: WO2010/126922, 2010, A1, . Location in patent: Page/Page column 62
[5] Zhurnal Organicheskoi Khimii, 1972, vol. 8, p. 803,804; engl. Ausg. S. 813, 814
[6] Patent: WO2013/33620, 2013, A1, . Location in patent: Page/Page column 68; 75
[7] Advanced Synthesis and Catalysis, 2018, vol. 360, # 5, p. 942 - 950
  • 2
  • [ 67-56-1 ]
  • [ 2365-85-7 ]
  • [ 369-26-6 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; for 12 h; Reflux To a stirred solution of 3-amino-4-fluoro-benzoic acid (25 g, 161 mmol) in methanol (300 mL) was added thionyl chloride (30 mL, 403 mmol) dropewise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-4-fluoro-benzoic acid methyl ester (27.5 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8FNO2 (M+H)+: 170.16, observed: 169.9
89% for 20 h; Reflux Step 1:
Preparation of methyl 3-amino-4-fluorobenzoate (54)
To a mixture of 3-amino-4-fluorobenzoic acid (1 g, 6.45 mmol) in MeOH (20 ml), conc. H2SO4 (0.687 ml, 12.89 mmol) was added drop wise, and the reaction was refluxed for 20 hours.
After cooling to room temperature the solvent was evaporated and the residue was partitioned between aq. NaHCO3 sat. sol.
and ethyl acetate; the organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness affording methyl 3-amino-4-fluorobenzoate as a brown solid (0.970 g, 5.73 mmol, 89percent yield, MS/ESI+170.0 [MH]+) (43)
290 mg Reflux 3-amino-4-fluorobenzoic acid (0.5g) was dissolved in methanol (lOml), then concentrated sulfuric acid (lml) was added. The reaction solution was heated to reflux until the reaction is complete. Then the reaction mixture was cooled down and poured into water, the pH of the resultant solution was adjusted to 8 by 2N NaOH solution. The product was extracted to EtOAc layer and the solvent was stripped off. 290mg of methyl 3-amino-4- fluorobenzoate was obtained.
Reference: [1] Patent: US2011/257151, 2011, A1, . Location in patent: Page/Page column 92
[2] Patent: US2014/155391, 2014, A1, . Location in patent: Paragraph 0392; 0393
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4436 - 4440
[4] Patent: WO2014/106019, 2014, A2, . Location in patent: Paragraph 0689; 0690
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2423 - 2435
  • 3
  • [ 456-22-4 ]
  • [ 369-26-6 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044
  • 4
  • [ 1007-16-5 ]
  • [ 369-26-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 3, p. 358 - 362
  • 5
  • [ 82702-31-6 ]
  • [ 369-26-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 3, p. 358 - 362
  • 6
  • [ 453-71-4 ]
  • [ 369-26-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 5, p. 942 - 950
[2] Patent: WO2013/33620, 2013, A1,
  • 7
  • [ 67-56-1 ]
  • [ 99-05-8 ]
  • [ 369-26-6 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 12, p. 4444 - 4446
  • 8
  • [ 2365-85-7 ]
  • [ 77-78-1 ]
  • [ 369-26-6 ]
Reference: [1] Patent: DE3106111, 1981, ,
[2] Patent: DE3106111, 1981, ,
  • 9
  • [ 125568-76-5 ]
  • [ 109-89-7 ]
  • [ 369-26-6 ]
  • [ 125569-04-2 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044
[2] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044
  • 10
  • [ 125568-76-5 ]
  • [ 369-26-6 ]
  • [ 125568-88-9 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2034 - 2044
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