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[ CAS No. 496946-78-2 ] {[proInfo.proName]}

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Chemical Structure| 496946-78-2
Chemical Structure| 496946-78-2
Structure of 496946-78-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 496946-78-2 ]

CAS No. :496946-78-2 MDL No. :MFCD03095229
Formula : C10H6F3NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FYRRCNKOGMDNSI-UHFFFAOYSA-N
M.W : 229.16 Pubchem ID :17389891
Synonyms :

Calculated chemistry of [ 496946-78-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.26
TPSA : 53.09 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) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.41
Log Po/w (XLOGP3) : 3.19
Log Po/w (WLOGP) : 4.04
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 2.88
Consensus Log Po/w : 2.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.55
Solubility : 0.0639 mg/ml ; 0.000279 mol/l
Class : Soluble
Log S (Ali) : -3.98
Solubility : 0.0242 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.0644 mg/ml ; 0.000281 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 496946-78-2 ]

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 [ 496946-78-2 ]

* 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 [ 496946-78-2 ]
  • Downstream synthetic route of [ 496946-78-2 ]

[ 496946-78-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 127-17-3 ]
  • [ 163444-17-5 ]
  • [ 496946-78-2 ]
YieldReaction ConditionsOperation in experiment
65% With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate In N,N-dimethyl-formamide at 105℃; for 10 h; Inert atmosphere A mixture of 2-iodo-4-(trifluoromethyl)aniline (C34) (250 mg, 0.871 mmol), pyruvic acid (0.123 mL,1.74 mmol), (195 mg, 1.74 mmol), and palladium(ll) acetate (10 mg, 44 pmol) in dry N,N-dimethylformamide (10 mL) was degassed viavacuum / nitrogen purges and heated at 105 °C for 10 h. The reaction mixture was allowed to cool to room temperature and was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel chromatography, eluting with 10percent ethyl acetate in hexane, to give the title compound as a brown solid.Yield: 130 mg, 65percent. LCMS m/z 228.0 (M-H); 1H NMR (400 MHz, DMSO-d6) ö 13.27 (5,1H), 12.20 (5, 1H), 8.09 (5, 1H), 7.61 (d, J=8.7 Hz, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.25 (5,1 H).
1.15 g With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24 h; Inert atmosphere A mixture of 2.28 g of 2-iodo-4-trifluoromethyla- niline, 2.10 g of pyruvic acid, 2.67 g of DAI3CO, 89mg of palladium (II) acetate, and 25 ml of DMF was stirred for 24 hours at 1000 C. in nitrogen atmosphere. After the reaction mixture was cooled to room temperature, 25 ml of ethyl acetate and 50 ml of 5 M hydrochloric acid were added thereto, and extraction was performed three times by using ethyl acetate. The collected organic layer was washed with water and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were washed with chloroform, thereby obtaining 1.15 g of 5-trif- luoromethylindole-2-carboxylic acid (hereinafter, described as a “compound 7 of the present invention”).1H-NMR (DMSO-D5) ö: 13.24 (br s, 1H), 12.20 (br s, 1H), 8.08 (s, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.51 (dd, 1H, J8.8, 1.6 Hz), 7.24 (d, 1H, J=1.6 Hz)
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2722 - 2725
[2] Patent: WO2015/49616, 2015, A1, . Location in patent: Page/Page column 66; 67
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4385 - 4388
[4] Patent: US2007/88071, 2007, A1, . Location in patent: Page/Page column 16
[5] Patent: US2015/289512, 2015, A1, . Location in patent: Paragraph 1210; 1211
  • 2
  • [ 455-14-1 ]
  • [ 496946-78-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4385 - 4388
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2722 - 2725
[3] Patent: US2015/289512, 2015, A1,
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