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[ CAS No. 116293-90-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 116293-90-4
Chemical Structure| 116293-90-4
Chemical Structure| 116293-90-4
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Product Details of [ 116293-90-4 ]

CAS No. :116293-90-4 MDL No. :MFCD08437578
Formula : C10H6FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WZTBLZIAYMSIOJ-UHFFFAOYSA-N
M.W : 191.16 Pubchem ID :17039616
Synonyms :

Calculated chemistry of [ 116293-90-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.66
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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.47
Log Po/w (XLOGP3) : 1.81
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 0.65
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 1.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.63
Solubility : 0.45 mg/ml ; 0.00235 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.628 mg/ml ; 0.00329 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.36
Solubility : 0.0842 mg/ml ; 0.000441 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 116293-90-4 ]

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

Application In Synthesis of [ 116293-90-4 ]

* 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.

  • Downstream synthetic route of [ 116293-90-4 ]

[ 116293-90-4 ] Synthesis Path-Downstream   1~17

  • 2
  • [ 116293-90-4 ]
  • [ 75-65-0 ]
  • [ 742698-99-3 ]
YieldReaction ConditionsOperation in experiment
56% With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; for 1h;Heating / reflux; A solution of 6-fluoro-quinoline-3-carboxylic acid (1.7 g, 8.89 mmol), diphenylphosphoryl azide (2.3 mL, 10.7 mmol) and diisopropylethylamine (4. 65 mL, 26.67 mmol) in t-butanol (40 mL) was heated at reflux for 1 hour. The solution was cooled to room temperature, and the solvent was evaporated in vacuo. The residue was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was dried over sodium sulfate, and the product was preabsorbed onto silica gel. Purification by flash chromatography, using a gradient of ethyl acetate (0% to 30%) in heptane as the eluant, to give the product as a colorless solid, 1.3 g (56%). MS: m/z 263.0 (MH+).
  • 3
  • [ 71083-14-2 ]
  • [ 116293-90-4 ]
YieldReaction ConditionsOperation in experiment
92% 3 N aqueous sodium hydroxide (5 mL, 15 mmol) was added to a solution of 6-fluoro-quinoline-3-carboxylic acid ethyl ester (2.2 G, 10 mmol) in methanol (50 mL). A heavy precipitate developed, and the mixture was diluted with an additional 50 mL of methanol to facilitate stirring. The mixture was stirred for 3 hours, then neutralized with of 1 N hydrochloric acid (15 mL). The methanol was evaporated in vacuo, and the slurry diluted with water. The product was collected by filtration and washed with water, to give the product, 1.76 g (92%) as a colorless solid. MS: m/z 192. 1 (MH+).
74% NaOH (aq, 2M, 8 mL, 16 mmol) was added to a mixture of 6-fluoroquinoline-3- carboxylic acid ethyl ester (927 mg, 4.23 mmol; see step (d) above), MeOH (15 mL) and dioxane (10 mL). The mixture was stirred at rt for 30 min, acidified with HCl (2M, 12 mL) and extracted with EtOAc (3x20 mL). The combined extracts were dried (Na2SO4) and concentrated to give the title compound (600 mg, 74%) as a light yellow solid.1H NMR (DMSO-J6, 400 MHz) δ 9.26 (IH, d), 8.96 (IH, d), 8.15 (IH, dd), 8.01 (IH, dd), 7.81 (IH, ddd).
With water; lithium hydroxide; In tetrahydrofuran; at 23℃; for 4h; To a stirred solution of compound C (2.6 g, 11.9 mmol, 1 eq) in THF (60 mL) was added LiOH (1.5 g, 35.6 mmol, 3 eq) in water (10 mL) drop wise at 0 C and the resulting mixture was stirred for 4 h at 23 C. The reaction mixture was concentrated in vacuo and the residue was diluted with water. The aqueous part was washed with ethyl acetate (20 mL) and then acidified with saturated aq. citric acid solution to pH 5. The organic components were extracted with ethyl acetate (200 mL), ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the compound D (2.2 g, 97%) as gummy material which was used in the next step without further purification. (0265) [0254] H NMR (400 MHz, DMSO-ifc) δ 9.28 (d, / = 2 Hz, 1 H), 8.97 (d, / = 2 Hz, 1 H), 8.19-8.15 (m, 1 H), 8.04-8.01 (m, 1 H), 7.85-7.79 (m, 1 H); (0266) [0255] LCMS: m/z = 192.1 [M+H], RT = 2.69 minutes; (Program Rl, Column Y).
  • 4
  • [ 116293-90-4 ]
  • 6-fluoroquinolin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% A mixture of -fluoroquinoline-S-carboxylic acid (595 mg, 3.11 mmol; see step (e) above), diphenylphosphoryl azide (991 mg, 3.6 mmol)5 triethylamine (364 mg, 3.6 mmol) and anhydrous THF (15 mL) was heated at reflux for 2 h. Water (5 mL) was added and the mixture was heated at reflux for 2 h. After cooling to rt, the mixture was extracted with EtOAc (3x15 mL) and the combined extracts dried (Na2SO4) and concentrated. The residue was recrystallised from toluene to give title compound (142 mg, 28 %) as a yellow solid.1H NMR (DMSO-J6, 400 MHz) δ 8.40 (IH, d), 7.79 (IH, dd), 7.38 (IH5 dd), 7.17 (IH5 dt), 7.09 (IH, d), 5.82 (2H, s).
  • 5
  • [ 1411771-65-7 ]
  • [ 116293-90-4 ]
  • [ 1411770-39-2 ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 40℃; for 16h; EXAMPLE 4(6-Fluoroquinolin-3-yl)(4-(4-methyl-6-(4-(trifluoromethyl)pyridin-2-ylamino)-2,3'-bipy ylamino)piperidin- 1 -yl)methanone; 4-Methyl-N6'-(piperidin-4-yl)-N6-(4-(trifluoromethyl)pyridin-2-yl)-2,3,-bipyridine-6,^ (30 mg, 0.07 mmol) was dissolved in DMF (500 uE). The solution was then treated with DIE A (24 μ, 0.14 mmol), <strong>[116293-90-4]6-fluoroquinoline-3-carboxylic acid</strong> (20 mg. 0.11 mmol), and 2,4,6- tripropyl-l,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (42 μ,, 0.07 mmol). The reaction was warmed to 40 C and stirred for 16 hours. The reaction was allowed to cool to room temperature. The mixture was diluted with DMSO (1.0 mL) and purfied by mass-triggered reverse phase high pressure liquid chromatography, eleuting with a 1% ammonium hydroxide buffered water/acetonitrile gradient over a Waters X-Bridge C-18 column, to afford (6- fluoroquinolin-3-yl)(4-(4-methyl-6-(4-(trifluoromethyl)pyridin-2-ylamino)-2 '-bipyridi ylamino)piperidin-l -yl)methanone. MS ESI calc'd. for C32H28F4N70 [M+H]+ 602, found 602. 1H NMR (600 MHz, DMSO-d6) δ 10.05 (s, IH), 8.87 (d, J = 2.0 Hz, IH), 8.66 (d, J = 2.1 Hz, IH), 8.60 (s, IH), 8.44 (d, J = 5.2 Hz, IH), 8.42 (d, J = 1.8 Hz, IH), 8.11 (dd, J = 5.4, 9.2 Hz, IH), 8.00 (dd, J = 2.4, 8.8 Hz, IH), 7.86 (dd, J = 2.9, 9.3 Hz, IH), 7.73 (m, IH), 7.20 (s, IH), 7.14 (d, J = 5.1 Hz, IH), 7.07 (s, IH), 6.87 (d, J = 7.6 Hz, IH), 6.56 (d, J = 8.8 Hz, IH), 4.37 (s, IH), 4.06 (s, IH), 3.32 (s, IH), 2.47 - 2.45 (m, IH), 2.27 (s, 3H), 2.04 (s, IH), 1.90 (s, IH), 1.49 (s, IH), 1.42 (s, 2H) . rhSyk IC50 = 8 nM.
  • 6
  • [ 944344-38-1 ]
  • [ 116293-90-4 ]
  • 6-fluoro-N-(3-hydroxy-4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)quinoline-3-carboxamide [ No CAS ]
  • 7
  • [ 944344-37-0 ]
  • [ 144-62-7 ]
  • [ 116293-90-4 ]
  • N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)-3-hydroxybutyl)-6-fluoroquinoline-3-carboxamide oxalic acid [ No CAS ]
  • 8
  • [ 116293-90-4 ]
  • [ 21103-33-3 ]
  • 6-fluoro-N-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butyl)quinoline-3-carboxamide [ No CAS ]
  • 9
  • [ 144-62-7 ]
  • [ 116293-90-4 ]
  • [ 189061-44-7 ]
  • N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl)-6-fluoroquinoline-3-carboxamide oxalic acid [ No CAS ]
  • 10
  • [ 395-81-3 ]
  • [ 116293-90-4 ]
  • 11
  • [ 116293-90-4 ]
  • C10H5FN2O [ No CAS ]
  • 12
  • [ 116293-90-4 ]
  • [ 742698-99-3 ]
  • 13
  • [ 116293-90-4 ]
  • 3-amino-6-fluoro-1-methylquinolin-1-ium iodide [ No CAS ]
  • 14
  • [ 116293-90-4 ]
  • [ 1398583-91-9 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; In dichloromethane; at 0 - 23℃; for 4h; To a stirred solution of compound D (2.2g, 11.5 mmol, 1 eq) in dry CH2CI2 (100 mL) was added oxalyl chloride (8.77 g, 69.1 mmol, 6 eq) drop wise at 0 C and the resulting mixture was stirred for 4 h at 23 C. The reaction mixture was concentrated in vacuo under nitrogen atmosphere to obtain the compound E (2.4 g) as colorless liquid which was used in the next step without further purification.
  • 15
  • [ 116293-90-4 ]
  • 6-fluoroquinoline-3-carboxylic acid methoxy(methyl)amide [ No CAS ]
  • 16
  • [ 116293-90-4 ]
  • cyclopropyl(6-fluoroquinolin-3-yl)methanone [ No CAS ]
  • 17
  • [ 116293-90-4 ]
  • cyclopropyl-C-(6-fluoroquinolin-3-yl)methylamine [ No CAS ]
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