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[ CAS No. 659729-09-6 ] {[proInfo.proName]}

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Chemical Structure| 659729-09-6
Chemical Structure| 659729-09-6
Structure of 659729-09-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 659729-09-6 ]

CAS No. :659729-09-6 MDL No. :MFCD09839523
Formula : C11H6ClF3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :RYYMGPDAXCLXSL-UHFFFAOYSA-N
M.W : 258.63 Pubchem ID :16747837
Synonyms :

Calculated chemistry of [ 659729-09-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.09
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.48
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 3.71
Log Po/w (WLOGP) : 4.97
Log Po/w (MLOGP) : 2.83
Log Po/w (SILICOS-IT) : 4.06
Consensus Log Po/w : 3.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.17
Solubility : 0.0174 mg/ml ; 0.0000674 mol/l
Class : Moderately soluble
Log S (Ali) : -3.94
Solubility : 0.0295 mg/ml ; 0.000114 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.67
Solubility : 0.000547 mg/ml ; 0.00000211 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 659729-09-6 ]

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 [ 659729-09-6 ]

* 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 [ 659729-09-6 ]
  • Downstream synthetic route of [ 659729-09-6 ]

[ 659729-09-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1193-21-1 ]
  • [ 128796-39-4 ]
  • [ 659729-09-6 ]
YieldReaction ConditionsOperation in experiment
49% With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 16 h; Inert atmosphere General procedure: All solvents and solutions used for this reaction were sparged with argonfor 15 minutes. In a round-bottomed flask was dissolved 4,6-dichloropyrimidine (1.5 equiv.) inTHF (1 M), under argon atmosphere. The arylboronic acid (1.0 equiv.), palladium acetate (0.02equiv., 2 molpercent), triphenylphosphine (0.04 equiv., 4 molpercent) and 1 M aqueous Na2CO3 solution(2.0 equiv.) were added and the mixture was stirred at 60 °C, overnight. After cooling to roomtemperature, the aqueous layer was extracted with Et2O and the organic layers were combined,washed with brine, dried over MgSO4, filtered and evaporated under vacuum. The crude materialwas purified by flash column chromatography to obtain the desired product.
47.2% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 120℃; for 8 h; Inert atmosphere; Sealed tube 2 g (0.011 mol) of 4-trifluoromethylbenzeneboronic acid was weighed out,4,6-dichloropyrimidine (1.60 g, 0.011 mol)Tetrakis (triphenyl palladium 0.15g with 2.5 g of anhydrous sodium carbonate was placed in a 120 mL sealed tube,A mixture of tetrahydrofen sitan 30 mL and 20 mL of deionized water was placed in a sealed tube as a solvent, and a stirrer was added and the stopper was capped.The whole device was purged with nitrogen for 3 to 4 times, placed in an oil bath and heated to 120 ° C for about 8 hours with stirring on a magnetic stirrer.After completion of the reaction, the sealing tube was cooled to room temperature, and the solution in the sealed tube was placed in a rotary vial, and the tetrahydrofuran solvent was distilled off under reduced pressure by rotary evaporator. And then extracted with ethyl acetate and water organic products 3 ~ 4 times, vacuum distillation solvent to petroleum ether: ethyl acetate 10: 1 will be steamed after the productionThe samples were separated by column chromatography and separated by separate column chromatography using dichloromethane to give about 1.28 g of a white solid in 47.2percent yield.
2.7 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 130℃; for 7 h; Example 21 2-[(4-Fluoro-benzenesulfonyl)-methyl-amino]-N-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4- ylmethyl] - acetamide A solution of 4-(trifluoromethyl)phenylboronic acid (5.0 g, 25.8 mmol), 4,6-dichloropyrimidine (3.92 g, 25.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (362 mg, 516 μιηο) and sodium carbonate (8.2 g, 77.4 mmol, Eq: 3) in a three solvent mixture of 50 mL DME, 7.5 mL ethanol and 7.5 mL water was heated at 130°C for 7 h. Upon cooling to rt, the reaction mixture was poured into saturated aqueous ammonium chloride solution and extracted with three times with ethyl acetate. The combined organic layers were washed with water and brine and dried over Na2S04. Filtration followed by removal of volatiles under reduced pressure gave a dark red solid. The mixture was purified by flash chromatography (5percent diethyl ether in hexane) to give 4-chloro-6-(4-trifluoromethyl- phenyl)-pyrimidine(2.76g) as a white solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 299 - 302
[2] Patent: CN106632488, 2017, A, . Location in patent: Paragraph 0167-0169
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3497 - 3514
[4] Patent: US2006/241296, 2006, A1, . Location in patent: Page/Page column 27
[5] Patent: WO2010/134478, 2010, A1, . Location in patent: Page/Page column 165
[6] Patent: WO2014/49047, 2014, A1, . Location in patent: Page/Page column 63
[7] Patent: WO2015/28989, 2015, A1, . Location in patent: Page/Page column 86
  • 2
  • [ 1193-21-1 ]
  • [ 128796-39-4 ]
  • [ 659729-09-6 ]
  • [ 697739-37-0 ]
Reference: [1] Patent: WO2004/46133, 2004, A1, . Location in patent: Page 40
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