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[ CAS No. 158063-66-2 ] {[proInfo.proName]}

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Chemical Structure| 158063-66-2
Chemical Structure| 158063-66-2
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Product Details of [ 158063-66-2 ]

CAS No. :158063-66-2 MDL No. :MFCD00082626
Formula : C7H4F3NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :LMRJHNFECNKDKH-UHFFFAOYSA-N
M.W : 191.11 Pubchem ID :2777549
Synonyms :

Calculated chemistry of [ 158063-66-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.2
TPSA : 50.19 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) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.91
Log Po/w (XLOGP3) : 1.26
Log Po/w (WLOGP) : 2.95
Log Po/w (MLOGP) : -0.02
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.79 mg/ml ; 0.00937 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 2.34 mg/ml ; 0.0122 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.29
Solubility : 0.985 mg/ml ; 0.00515 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 158063-66-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 158063-66-2 ]

* 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 [ 158063-66-2 ]
  • Downstream synthetic route of [ 158063-66-2 ]

[ 158063-66-2 ] Synthesis Path-Upstream   1~14

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  • [ 198401-76-2 ]
Reference: [1] Patent: WO2006/102535, 2006, A2, . Location in patent: Page/Page column 67-68
  • 2
  • [ 158062-71-6 ]
  • [ 158063-66-2 ]
YieldReaction ConditionsOperation in experiment
99.1% With sodium hydroxide In water at 100℃; for 4 h; At room temperature, into 250 ml of a flask containing 1.5 g of Pd/MCM-22 catalyst, 9.5 g of 4-trifluoromethylnicotinamide and 40 ml of an aqueous solution of 25percent sodium hydroxide were added in sequence. The reaction solution was heated to 100 ° C, and the reaction was kept for 4 hours. The solid was dissolved and turned into a pale yellow clear solution. After the reaction was completed, the mixture was cooled to room temperature, adjusted to pH = 2 with concentrated hydrochloric acid, stirred, suction filtered, and the residue was washed with water and dried. White powdery solid 4-trifluoromethylnicotinic acid.
89.7%
Stage #1: for 5 h; Heating / reflux
Stage #2: With sodium carbonate In water
(Reference Example 14)
4-Trifluoromethylnicotinic acid (Compound VIII)
5 ml of 35percent concentrated hydrochloric acid (10ml, 57 mmol) was added to 4-trifluoromethylnicotinamide (90 g, 10 mmol), and the mixture was heated under reflux for 5 hours..
water (50 ml) was added, and the mixture was adjusted to PH 3 using sodium carbonate, and then extracted with ethyl acetate twice..
The organic layers were combined, dried over magnesium sulfate and then concentrated under reduced pressure to obtain 1.71 g (yield 89.7percent) of the title compound.1H-NMR spectrum (500 MHz, DMSO-d6) δ (ppm) 14.07 (1H, brd.s), 9.08 (1H, s), 9.00 (1H, d, J=5.2Hz), 7.89 (1H, d, J=5.2Hz).
Reference: [1] Patent: CN108586328, 2018, A, . Location in patent: Page/Page column 4-7
[2] Patent: EP1460071, 2004, A1, . Location in patent: Page 40
  • 3
  • [ 13600-43-6 ]
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YieldReaction ConditionsOperation in experiment
90.1% With sodium hydroxide In ethanol at 80℃; for 10 h; Inert atmosphere Under nitrogen protection 100 g (581 mmol) of 3-cyano-4-trifluoromethylpyridine,310g 30wtpercent NaOH ethanol solution,700 mL of EtOH was placed in a three-neck reaction flask with a reflux condenser and stirred at 80 ° C for 10 hours. Most of the EtOH was removed by distillation under reduced pressure, and then 1 L of ethyl acetate and 1 L of water were taken and washed. After removal of the organic phase, the aqueous phase is left and acidified to pH less than 1 with concentrated hydrochloric acid. After extracting 1 L of ethyl acetate for 3 times, the organic phase was concentrated to obtain 100 g (523 mmol) of 4-trifluoromethylnicotinic acid solid in a yield of 90.1percent.
84%
Stage #1: With potassium hydroxide; water In water; ethylene glycol at 200℃; for 4 h;
Stage #2: With hydrogenchloride In water; ethylene glycol at 20℃;
(Reference Example 15)
4-Trifluoromethylnicotinic acid (Compound VIII)
3-Cyano-4-trifluoromethylpyridine (11.47 g, 66.64 mmol) was suspended in ethylene glycol (76 ml) and 85percent potassium hydroxide (13.20 g, 200 mol) was added..
The mixture was stirred under heating at 20°C for 4 hours..
The reaction solution was cooled to room temperature and then water (50 ml) and 4N hydrochloric acid (60 ml) were added..
The resulting reaction mixture was extracted with ethyl acetate four times..
The organic layers were combined, washed with saturated salt water, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 10.70g (yield 84.0percent) of the title compound.
Reference: [1] Patent: CN108191749, 2018, A, . Location in patent: Paragraph 0029; 0052; 0057; 0073; 0079
[2] Patent: EP1460071, 2004, A1, . Location in patent: Page 40; 41
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  • [ 60838-50-8 ]
  • [ 120417-45-0 ]
  • [ 158063-66-2 ]
YieldReaction ConditionsOperation in experiment
45.3%
Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3.33333 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
(Reference Example 16)
4-Trifluoromethylnicotinic acid (Compound VIII)
To a suspension of sodium hydride (60percent dispersion in mineral oil, 0.40 g, 10 mmol) in 10 ml of tetrahydrofuran, a tetrahydrofuran (2 ml) solution of 4-amino-1,1,1-trifluoromethyl-3-buten-2-one (1.39 g, 10 mmol) and 3-methoxyacrylonitrile (0.83 g, 10 mmol) was gradually added under ice-cooling..
The mixture was stirred at the same temperature for 20 minutes and then stirred at room temperature for 3 hours..
To the reaction mixture, concentrated hydrochloric acid (1.2 ml) was added and then the solvent was removed under reduced pressure..
ethyl acetate was added to the resulting residue..
The organic layer was washed with brine twice, dried over magnesium sulfate and then concentrated..
The residue was dissolved in methanol (20 ml) and 28percent sodium methoxide (1.93 g, 10.0 mmol) was added..
The mixture was refluxed for 3 hours..
After removing methanol under reduced pressure, an 8N aqueous sodium hydroxide solution (5 ml, 40.0 mmol) was added to the reaction solution..
The reaction mixture was refluxed for 5 hours, then poured into water, and the aqueous layer was washed with diethyl ether..
The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate twice..
The obtained organic layer was washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure to obtain 866 mg (yield 45.3percent) of the title compound.
Reference: [1] Patent: EP1460071, 2004, A1, . Location in patent: Page 41
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  • [ 22398-14-7 ]
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YieldReaction ConditionsOperation in experiment
49%
Stage #1: With sodium hydride In 1-methyl-pyrrolidin-2-one at 0 - 10℃; for 1 h;
Stage #2: at 65℃; for 7 h;
Stage #3: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; methanol; water for 9 h; Reflux
In a 500 ml flask, 100 mL of 1-methylpyrrolidone and 2.9 g of sodium hydride were added, and the mixture was cooled to 0 ° C. while stirring, and droppedPlus 1,1,1-trifluoro-4-aminobutenone 10 g, the control temperature below 10 , the reaction for 1 hour,Dimethyl 2-methoxymethylenemalonate was added12.5g, the reaction for 4 hours.Then, 200 mL of methanol was added and heated to 65 ° C. After reacting for 3 hours, 300 g of concentrated hydrochloric acid (30percent wt) was added and heated to boiling for 9 hours under reflux. The methanol was distilled off, 300 g of ice water was added, Washed with water and dried to give 6.8 g of a yellow solid in 49percent yield, as a yellow solid.
Reference: [1] Patent: CN107298653, 2017, A, . Location in patent: Paragraph 0030; 0031; 0033
  • 6
  • [ 590371-81-6 ]
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Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 7
  • [ 3796-24-5 ]
  • [ 124-38-9 ]
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Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575
  • 8
  • [ 124-38-9 ]
  • [ 625115-02-8 ]
  • [ 158063-66-2 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575
  • 9
  • [ 503437-19-2 ]
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Reference: [1] Patent: CN107286086, 2017, A, . Location in patent: Paragraph 0021; 0023; 0029
  • 10
  • [ 81565-18-6 ]
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Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1559 - 1568
  • 11
  • [ 3796-24-5 ]
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Reference: [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575
  • 12
  • [ 13600-42-5 ]
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Reference: [1] Patent: CN107286086, 2017, A,
[2] Patent: CN108191749, 2018, A,
  • 13
  • [ 158063-66-2 ]
  • [ 81565-19-7 ]
Reference: [1] Patent: CN108892638, 2018, A, . Location in patent: Paragraph 0017; 0019; 0020; 0021; 0023; 0025; 0027; 0029
  • 14
  • [ 158063-66-2 ]
  • [ 158062-71-6 ]
Reference: [1] Patent: US5360806, 1994, A,
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