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Chemical Structure| 42017-89-0
Chemical Structure| 42017-89-0
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Product Details of [ 42017-89-0 ]

CAS No. :42017-89-0 MDL No. :MFCD00792461
Formula : C17H15ClO4 Boiling Point : -
Linear Structure Formula :- InChI Key :MQOBSOSZFYZQOK-UHFFFAOYSA-N
M.W : 318.75 Pubchem ID :64929
Synonyms :
FNF acid;NSC 281318;Procetofenic acid;Trilipix

Calculated chemistry of [ 42017-89-0 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.18
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 84.05
TPSA : 63.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 3.91
Log Po/w (WLOGP) : 3.81
Log Po/w (MLOGP) : 2.86
Log Po/w (SILICOS-IT) : 3.78
Consensus Log Po/w : 3.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.35
Solubility : 0.0141 mg/ml ; 0.0000443 mol/l
Class : Moderately soluble
Log S (Ali) : -4.94
Solubility : 0.00362 mg/ml ; 0.0000114 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.00128 mg/ml ; 0.00000402 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 42017-89-0 ]

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 [ 42017-89-0 ]

* 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 [ 42017-89-0 ]
  • Downstream synthetic route of [ 42017-89-0 ]

[ 42017-89-0 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 1159999-13-9 ]
  • [ 42017-89-0 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With potassium hydroxide In ethanol for 16 h; Heating / reflux
Stage #2: With hydrogenchloride In water
To a solution of 104 (5.00 g, 12.2 mmol) in ethanol (150 mL) was added a solution of potassium hydroxide (2.74 g, 48.9 mmol) in ethanol (50 mL) and the reaction mixture was heated at reflux and stirred for 16 h. Ethanol was removed under vacuum and water (200 mL) was added. The aqueous solution was washed with diethyl ether (2 x 100 mL) and acidified to pH 1 with 2 N HCl. The acidic aqueous solution was then extracted with ethyl acetate (2 x 150 mL) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide 105 (3.57 g, 91percent) as an off-white solid: 1H NMR (300 MHz, CD3OD) δ 7.75-7.70 (m, 4H), 7.52 (d, J = 8.6 Hz, 2H), 6.96 (d, J = 9.0 Hz, 2H), 1.65 (s, 6H).
Reference: [1] Patent: WO2009/73138, 2009, A2, . Location in patent: Page/Page column 81-82
  • 2
  • [ 67-66-3 ]
  • [ 42019-78-3 ]
  • [ 67-64-1 ]
  • [ 42017-89-0 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: for 2 h; Heating / reflux
Stage #2: for 8 h; Heating / reflux
A mixture of 4-chloro-4'-hydroxybezophenone (116 g, 0.500 mole) and sodium hydroxide (120 g, 3.00 mole) in acetone (1 L) was heated to reflux for 2 hours. The heating was stopped and the heating source was removed. A mixture of chloroform (179 g, 1.50 mole) in acetone (300 mL) was added drop-wise. The reaction mixture was stirred overnight without heating. The mixture was heated to reflux for 8 hours and then allowed to cool to room temperature. The precipitate was removed by filtration and washed with acetone (100 mL). The filtrate was concentrated under reduced pressure to give a brown oil. Water (200 mL) was added to the brown oil and was acidified (to pH=l) with IN hydrochloric acid. The precipitate, which formed was filtered and dried under high vacuum. The remaining yellow solid (268 g) was recrystallized from toluene in 4 batches (400 mL toluene each). After filtration and drying under high vacuum, the experiment produced fenofibric acid (116 g, 73percent yield) as a light yellow solid. 'H NMR (300 MHz, DMSO-d6): 6 = 13.22 (1H, s, br), 7.72 (4H, d, J= 8.4 Hz), 7.61 (2H, d, J= 7. 8 Hz), 6.93 (2H, d, J= 7. 8 Hz), 1.60 (6H, s). "C NMR (75 MHz, DMSO-d6) : 5 = 192.96, 174.18, 159.35, 136.84, 136.12, 131.67, 131.02, 129.12, 128. 43, 116. 91,78. 87,25. 13.
Reference: [1] Patent: WO2005/46575, 2005, A2, . Location in patent: Page/Page column 176-177
[2] Chem.Abstr., 1976, vol. 85, # 192382,
  • 3
  • [ 42019-08-9 ]
  • [ 42017-89-0 ]
YieldReaction ConditionsOperation in experiment
0.95 g With water; sodium hydroxide In ethanol at 25℃; 2) Diluted with 32mL ethanol in the concentrated residue.Temperature control to 25°CTo dissolve the system,Then add 1mol/L sodium hydroxide aqueous solution 10mL, keep warm until reaction is complete,Vacuum filtration,The filtrate was slowly adjusted to pH 4 with 6M hydrochloric acid.Stirring and crystallization,Vacuum filtration,The filter cake was washed with 30 mL water.Vacuum dryingThat is, crude 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropionic acid;3) Add the above 2.0g crude product to a 50mL single-mouth bottle, add 30mL acetone, stir and heat to reflux to dissolve,Incubate for 0.5 hour, stop heating, naturally cool to room temperature, crystallize for 8 hours, filter under reduced pressure, filter cake rinse with a little acetone, 55°C vacuum drying, an off-white solid.Add the above white solid 1.2g to a 50mL single-mouth bottle, add 18mL of ethyl acetate, stir and heat backFlow to dissolve, keep warm for 0.5 hour, stop heating, heat filter, naturally cool the filtrate to room temperature, crystallize for 8 hours, filter under reduced pressure, filterThe cake was rinsed with a small amount of ethyl acetate and dried under vacuum at 55° C. to give 0.95 g of an off-white solid, ie 2-[4-(4-chlorobenzoyl)phenoxyBase]-2-methylpropionic acid refined product, purity 99.92percent.
Reference: [1] Patent: CN107698422, 2018, A, . Location in patent: Paragraph 0024-0027; 0031-0035; 0037-0039; 0043-0045
  • 4
  • [ 2052-01-9 ]
  • [ 42019-78-3 ]
  • [ 42017-89-0 ]
Reference: [1] Synthesis, 2004, # 12, p. 1959 - 1962
[2] Journal of the Chinese Chemical Society, 2007, vol. 54, # 3, p. 575 - 578
  • 5
  • [ 49562-28-9 ]
  • [ 42017-89-0 ]
YieldReaction ConditionsOperation in experiment
15%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuranReflux
Stage #2: With hydrogenchloride In tetrahydrofuran; water
Example 12 - Formula 139 - Compounds 12a 12bIntermediate B: 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid To a stirred solution of compound A (1 .0 g, 2.77 mmol) in THF (10 mL) was added LiOH-H&20 (0.7 g, 16.6 mmol) and H20 (10 mL). The resulting mixture was heated at reflux overnight then quenched with a 1 M aqueous HCI solution and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine, dried over MgS04 and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH, 15/1 , v/v) to give 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (130 mg, 15percent) as a white solid.LC-MS (Agilent): Rt 3.00 min; m/z calculated for Ci7H15CI04 [M+H]+ 319.07, found 319.1 .
15% With lithium hydroxide monohydrate; water In tetrahydrofuranReflux To a stirred solution of compound A (1.0 g, 2.77 mmol) in THF (10 mL) was added LiOH.H2O (0.7 g, 16.6 mmol) and H2O (10 mL).
The resulting mixture was heated at reflux overnight then quenched with a 1 M aqueous HCl solution and extracted with EtOAc (10 mL*3).
The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure.
The residue was purified by flash chromatography (CH2Cl2/MeOH, 15/1, v/v) to give 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoic acid (130 mg, 15percent) as a white solid.
LC-MS (Agilent): Rt 3.00 min; m/z calculated for C17H15ClO4 [M+H]+ 319.07. found 319.1.
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 14, p. 2497 - 2499
[2] Acta Crystallographica Section C: Crystal Structure Communications, 2005, vol. 61, # 2, p. o81-o84
[3] Patent: WO2012/63085, 2012, A2, . Location in patent: Page/Page column 83-84
[4] Patent: US2013/225594, 2013, A1, . Location in patent: Paragraph 0268; 0269
[5] Photochemistry and Photobiology, 2002, vol. 75, # 3, p. 193 - 200
[6] Biochemical Pharmacology, 2004, vol. 67, # 2, p. 285 - 292
[7] Farmaco, 2005, vol. 60, # 5, p. 425 - 438
[8] Crystal Growth and Design, 2014, vol. 14, # 8, p. 3800 - 3812
[9] Drug Metabolism and Disposition, 2015, vol. 43, # 11, p. 1815 - 1822
  • 6
  • [ 122-01-0 ]
  • [ 42017-89-0 ]
Reference: [1] Chem.Abstr., 1976, vol. 85, # 192382,
  • 7
  • [ 100-66-3 ]
  • [ 42017-89-0 ]
Reference: [1] Chem.Abstr., 1976, vol. 85, # 192382,
  • 8
  • [ 42017-89-0 ]
  • [ 67-48-1 ]
  • [ 856676-23-8 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With triethylamine In ethanol
Stage #2: Reflux
Charge 10 gm fenofibric acid and 90 ml absolute ethanol and 4.5 ml triethylamine in to 250 ml RBF. Stir it for 10-15 minutes to get clear solution. Charge in to 250 ml RBF and charge 4.4 gm choline chloride. Heat it up to reflux temperature to get clear solution. Filter it through hyflo bed and wash it with absolute ethanol (10 ml). Cool it up to ambient temperature. Stir it for 12-15 hours at ambient temperature. Cool it at 0-5° C and stir for 2 hours at 0-5° C. Filter it and suck dry it. Charge wet cake in to 250 ml RBF and 50 ml absolute ethanol. Stir it for one hour at ambient temperature. Filter it and wash it with 10 ml absolute ethanol. Dry it at 50-60° C. Dry wt. - 8.0 gm (yield: -75percent).
75%
Stage #1: With triethylamine In ethanol for 10 - 15 h;
Stage #2: Reflux
Example-1
Preparation of Choline Salt of Fenofibric Acid
Charge 10 gm fenofibric acid and 90 ml absolute ethanol and 4.5 ml triethylamine in to 250 ml RBF.
Stir it for 10-15 minutes to get clear solution.
Charge in to 250 ml RBF and charge 4.4 gm choline chloride.
Heat it up to reflux temperature to get clear solution.
Filter it through hyflo bed and wash it with absolute ethanol (10 ml).
Cool it up to ambient temperature.
Stir it for 12-15 hours at ambient temperature.
Cool it at 0-5° C. and stir for 2 hours at 0-5° C.
Filter it and suck dry it.
Charge wet cake in to 250 ml RBF and 50 ml absolute ethanol.
Stir it for one hour at ambient temperature.
Filter it and wash it with 10 ml absolute ethanol.
Dry it at 50-60° C. Dry wt.-8.0 gm (yield: ~75percent).
Reference: [1] Patent: WO2010/86700, 2010, A2, . Location in patent: Page/Page column 7
[2] Patent: US2011/288331, 2011, A1, . Location in patent: Page/Page column 3
  • 9
  • [ 42017-89-0 ]
  • [ 123-41-1 ]
  • [ 856676-23-8 ]
Reference: [1] Crystal Growth and Design, 2014, vol. 14, # 8, p. 3800 - 3812
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