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[ CAS No. 15084-51-2 ] {[proInfo.proName]}

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Chemical Structure| 15084-51-2
Chemical Structure| 15084-51-2
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Product Details of [ 15084-51-2 ]

CAS No. :15084-51-2 MDL No. :MFCD00007449
Formula : C10H13ClO2S Boiling Point : No data available
Linear Structure Formula :(((CH3)3C)C6H4)SO2Cl InChI Key :YEZADZMMVHWFIY-UHFFFAOYSA-N
M.W : 232.73 Pubchem ID :139882
Synonyms :

Calculated chemistry of [ 15084-51-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.8
TPSA : 42.52 ?2

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) : -5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 3.62
Log Po/w (WLOGP) : 3.99
Log Po/w (MLOGP) : 2.76
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 3.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.75
Solubility : 0.0415 mg/ml ; 0.000178 mol/l
Class : Soluble
Log S (Ali) : -4.2
Solubility : 0.0147 mg/ml ; 0.000063 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0162 mg/ml ; 0.0000698 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.68

Safety of [ 15084-51-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 15084-51-2 ]

* 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.

  • Downstream synthetic route of [ 15084-51-2 ]

[ 15084-51-2 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 15084-51-2 ]
  • [ 2133-34-8 ]
  • [ 201466-06-0 ]
  • 2
  • [ 15084-51-2 ]
  • [ 33084-49-0 ]
  • 4-tert-butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 39 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 5 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol)in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 39 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 45 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).

  • 3
  • [ 15084-51-2 ]
  • [ 24629-25-2 ]
  • [ 1032477-05-6 ]
  • 4
  • [ 15084-51-2 ]
  • [ 111628-39-8 ]
  • [ 695221-93-3 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine; In dichloromethane; at 0 - 20℃; for 6h; General procedure: 2-(Piperazin-1-yl)benzazolyl derivatives 8a-d (1 equivalent) and triethylamine (1.5 equivalents) were dissolved in 25 ml dry CH2Cl2 and cooled to 0C in an ice salt bath. Then the required phenylsulfonyl chloride (1.1 equivalents) dissolved in 20 ml dry CH2Cl2 was added dropwise. After the addition, the reaction mixture was stirred at 0C for a further 1h and then allowed to warm to room temperature and the course of the reaction followed by TLC. After completion, the mixture was diluted with additional 50 ml of CH2Cl2 and extracted with 10% NaHCO3 solution (3 x 50 ml). The organic phase was washed with dist. H2O, sat. NaCl solution, dried over anhyd. Na2SO4, filtered and evaporated to dryness. The product was recrystallised from the appropriate solvent, the precipitate formed was filtered under suction and dried at 60C under high vacuum.
  • 5
  • [ 15084-51-2 ]
  • [ 36936-23-9 ]
  • 4-(tert-butyl)-N-(5-chloro-6-methylpyridin-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With pyridine; In chloroform; at 0 - 100℃; for 12.0h; To a stirred solution of compound LXVIII (3 g, 21.12 mmol) in chloroform (60 ml) was addedpyridine (15 ml) at 0C followed by addition of 4-tert-butylbenzenesulfonyl chloride (XI, 5.89g, 25.34 mmol). The reaction mixture was heated at 100C for 12 h, cooled to room temperature and concentrated under reduced pressure. The crude material was diluted with a saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over anhydrous Na2SO4 and evaporated under reducedpressure to afford 4-(tert-butyl)-N-(5 -chloro-6-methylpyridin-2-yl)benzenesulfonamide(LXIX; 6 g, 84% yield). ?H NMR (400 MHz, DMSO-d6) oe 11.11 (bs, 1H), 7.86-7.84 (d, J8.4 Hz, 2H), 7.72-7.70 (d, J 8.8 Hz, 1H), 7.60-7.58 (d, J 8.4 Hz, 2H), 6.94-6.93 (d, J= 7.6Hz, 1H), 2.36 (s, 3H), 1.27 (s, 9H). MS (M+1): 339.2.
  • 6
  • [ 15084-51-2 ]
  • [ 1080-12-2 ]
  • (E)-2-methoxy-4-(3-oxobut-1-enyl)phenyl 4-tert-butylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In methanol; at 20℃; General procedure: Solutions of selected methyl ketones (2 mmol) in methanol(6 mL) were stirred and corresponding sulfonylchlorides (2.4 mmol) were added. Then, triethylamine(0.6 mL) was added dropwise. The mixtures were stirredovernight at room temperature. After completion of thereactions, mixtures were poured into iced water withstirring. In some cases (for our compounds 7f, 7g, 8e, 8f,8g, and 9g; see below), the formed precipitate was filteredand washed with cold diethyl ether. In other cases, whenno precipitate formed, the organic layer was extractedwith dichloromethane (3 × 50 mL), dried over anhydrousNa2SO4 and evaporated under vacuum. The residue waspurified by short column chromatography on silica gel,using dichloromethane as eluent. The oil obtained usuallycrystallized; if not, the oily residue was dissolved indiethyl ether from which products crystallized on standingin a deepfreeze. Crude products were washed with coldether, and 21 pure, mostly white crystals were obtained, asfollows:
  • 7
  • [ 15084-51-2 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-3-yl 4-(tert-butyl)benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.9% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 8
  • [ 15084-51-2 ]
  • [ 19008-43-6 ]
  • benzyl 4-((4-(tert-butyl)phenyl)sulfonamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% at 20℃; for 24h;Cooling with ice; Inert atmosphere; General procedure: The acid or sulfonyl chloride (1.0-1.1 equiv.) was added in one go to an ice-cooled solution of the appropriate amine or amine hydrochloride (1.0-1.1 equiv.) and diisopropylethylamine, triethylamine or pyridine (2.0-3.0 equiv.) in CH2Cl2 or chloroform (0.1-0.2M) and stirred at RT. After 24h, the reaction was quenched with 1M HCl. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered and concentrated in vacuo, and column chromatography isolated the target compound.
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; ;