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[ CAS No. 143062-84-4 ] {[proInfo.proName]}

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Chemical Structure| 143062-84-4
Chemical Structure| 143062-84-4
Structure of 143062-84-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 143062-84-4 ]

CAS No. :143062-84-4 MDL No. :MFCD01861147
Formula : C10H14FNO3S Boiling Point : -
Linear Structure Formula :- InChI Key :XUWZMHVPMZXIRU-LMLSDSMGSA-N
M.W : 247.29 Pubchem ID :53350313
Synonyms :

Calculated chemistry of [ 143062-84-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 58.45
TPSA : 88.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.18
Log Po/w (XLOGP3) : -1.35
Log Po/w (WLOGP) : 2.8
Log Po/w (MLOGP) : 1.3
Log Po/w (SILICOS-IT) : 0.64
Consensus Log Po/w : 0.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.73
Solubility : 45.6 mg/ml ; 0.184 mol/l
Class : Very soluble
Log S (Ali) : -0.01
Solubility : 239.0 mg/ml ; 0.967 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.13
Solubility : 1.83 mg/ml ; 0.00741 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.7

Safety of [ 143062-84-4 ]

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 [ 143062-84-4 ]

* 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.

  • Upstream synthesis route of [ 143062-84-4 ]
  • Downstream synthetic route of [ 143062-84-4 ]

[ 143062-84-4 ] Synthesis Path-Upstream   1~5

  • 1
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YieldReaction ConditionsOperation in experiment
204 g
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 60 h; Large scale
Stage #2: With palladium on activated charcoal; hydrogen In methanol for 24 h; Autoclave; Large scale
Stage #3: Large scale
(1) Take 1.32 kg dimethyl malonate and 3.7 kg 1,1,2-tribromo-2-fluoroethane were added into a 50L in three-mouth flask. Dissolve in 15L anhydrous dimethylformamide. The three-mouth flask was placed in a 25 °C water bath. Under even stirring, add in batches 4.4 kg anhydrous potassium carbonate and react for 60 hours. the reaction end after adding ice water 30L, then ethyl acetate (8L × 5) extraction, the combined organic phase, the organic phase is washed to neutral saturated sodium chloride aqueous solution, then dried with anhydrous sodium sulfate, the solvent evaporation, then the residue by adding 3L ethyl ether, stirring in ice bath 4 hours, the final filtering to obtain 1.7 kg solid A.
(2) The prepared solid A was added into a 10L hydrogenation autoclave. Add 6L methanol to dissolve. Then add 72g palladium-carbon as the catalyst. The hydrogen replaced the air in the autoclave 4 times. Under stirring conditions, continue to place hydrogen gas (5 atmospheric pressure) and react for 24 hours, filtering, solution concentrated to dry, the residue by adding 10L ethyl acetate, water washing (3L × 2), 2L saturated salt water washing, dried with anhydrous sodium sulfate, 78 °C to evaporate the solvent, get 898g B oily liquid.
(3) The prepared oily liquid B was added into a 20L reactor. Add 5L dimethylformamide, 184 mL distilled water and 299g sodium chloride to prepare a mixed solution. Reflux reaction for 35 hours. Reaction liquid was added 12L distilled water, then ethyl acetate (2.5L × 6) extraction, the combined organic phase, the organic phase after the water washing (2L × 3), 2L saturated salt water washing, dried with anhydrous sodium sulfate, 114 °C atmospheric dryness to obtain 506g solid C.
(4) The resulting solid C was added into a 10L reaction flask. Use 4L tetrahydrofuran and 2L distilled water to dissolve. Place in ice bath. Under stirring, add in batches 270g lithium hydroxide monohydrate. Maintan in ice water bath for 3 hours, then dropwise 4 mol/L hydrochloric acid to the reaction solution pH value is 2 - 3 the left and right, of the liquid, the resulting aqueous phase of ethyl acetate (1L × 3) extraction, the combined organic phase, 1L washing, 1L saturated salt water washing, dried with anhydrous sodium sulfate, concentrated, the residue dissolved in 0.5L ethyl acetate, stirring slowly dripping 4.5L petroleum ether, stirring at room temperature for 10 hours, filtering, washing the filter cake with petroleum ether, and a ground line to obtain 380g solid D.
(5) The resulting solid D was added into 5L reaction flask. Use 3L ethanol to dissolve. Under stirring conditions, add dropwise 425g L-leucinamide in ethanol solution 0.5L. Heat to 50 °C and continue stirring for 3 hours. Then the solution cooled to room temperature and continue to stir 3 hours, filtering, the filter cake is washed with ethanol, and a ground line, the filter cake is dissolved into to the 2.5L acetonitrile and 0.5L in ethanol mixed solution, heating to 50 °C stirring 2 hours, then cooled to room temperature stirring 2 hours, filtering, filters the cake second gradethe nitrile washes, and a ground line to obtain 364g solid E.
(6) The resulting solid E was disslved in 3L distilled water and placed in the ice bath. Under stirring condition slowly add dropwise 3 mol/L hydrochloric acid solution until the pH value is 2-3. Continue stirring for 1 hour. the solution after the reaction using methylene chloride (1L × 3) extraction, organic uses 0.5L saturated salt water washing, dried with anhydrous sodium sulfate, concentrated, the resulting residue is dissolved in the 0.25L ethyl acetate and 2.25L petroleum ether of the mixed solution, stirring at the room temperature 2 hours, filtering, by 149g solid F.
(7) The resulting solid F, 393 ml diphenylphosphoryl azide and 315 ml triethylamine were added into 3L reaction flask.Use 2L tert-butanol to dissolve. Under stirring reflux for 12 hours. the reaction solution concentration, adding 3L ethyl acetate extraction, the organic phase for sequentially 400 ml saturated ammonium chloride solution washing, 400 ml saturated sodium bicarbonate solution washing, 300 ml saturated salt water washing, dried with anhydrous sodium sulfate, filtered, to evaporate the solvent, the resulting residue is dissolved in 800 ml of petroleum ether and ethyl acetate 10:1 in mixed solution stirring 3 hours, filtering pumping job 167g solid G.
(8) The resulting solid G and 470g p-toluenesulfonic acid were dissolved in 3L acetonitrile. Stir at room temperature for 36 hours. concentrated, by adding 600 ml ethyl ether petroleum ether 1:1 mixed solution, stirring the reaction 3 hours, filtering pumping job 204g Sitafloxacin three membered ring intermediate (purity 99.2percent).
Reference: [1] Patent: CN104803857, 2017, B, . Location in patent: Paragraph 0038-0064
  • 2
  • [ 104-15-4 ]
  • [ 142977-51-3 ]
  • [ 143062-84-4 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 24, p. 3487 - 3490
[2] Tetrahedron, 1994, vol. 50, # 13, p. 3905 - 3914
  • 3
  • [ 104-15-4 ]
  • [ 156481-81-1 ]
  • [ 143062-84-4 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 13, p. 3905 - 3914
  • 4
  • [ 104-15-4 ]
  • [ 127199-16-0 ]
  • [ 143062-84-4 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 15, p. 7226 - 7231
  • 5
  • [ 104-15-4 ]
  • [ 143062-84-4 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 13, p. 3889 - 3904
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