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[ CAS No. 1450595-86-4 ] {[proInfo.proName]}

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Chemical Structure| 1450595-86-4
Chemical Structure| 1450595-86-4
Structure of 1450595-86-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1450595-86-4 ]

CAS No. :1450595-86-4 MDL No. :MFCD32858292
Formula : C20H21ClFN5O3S Boiling Point : -
Linear Structure Formula :- InChI Key :OJKONCJPCULNOW-DYVFJYSZSA-N
M.W : 465.93 Pubchem ID :71711862
Synonyms :
Chemical Name :5-Chloro-2-fluoro-4-(((1S,2R)-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl)oxy)-N-(pyrimidin-4-yl)benzenesulfonamide

Calculated chemistry of [ 1450595-86-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.35
Num. rotatable bonds : 6
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 114.06
TPSA : 107.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : 3.31
Log Po/w (WLOGP) : 5.22
Log Po/w (MLOGP) : 1.87
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 3.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.82
Solubility : 0.00699 mg/ml ; 0.000015 mol/l
Class : Moderately soluble
Log S (Ali) : -5.24
Solubility : 0.00268 mg/ml ; 0.00000574 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.76
Solubility : 0.0000802 mg/ml ; 0.000000172 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.26

Safety of [ 1450595-86-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1450595-86-4 ]

* 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 [ 1450595-86-4 ]

[ 1450595-86-4 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 1450598-94-3 ]
  • [ 1450595-86-4 ]
YieldReaction ConditionsOperation in experiment
99% With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 1h; 122.122c (122c) 5-Chloro-2-fluoro-4-[(1S,2R)-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide To a solution of the 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-[(1S,2R)-2-(1-methyl-1H-pyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide (0.371 g, 0.602 mmol) prepared in Example 122b and triethylsilane (0.48 mL, 3.01 mmol) in dichloromethane (6.0 mL), trifluoroacetic acid (0.60 mL) was added at room temperature, and the reaction solution was stirred for 1 hour. The reaction solution was concentrated, and the residue was purified with silica gel chromatography (ethyl acetate/methanol=6:1) to yield the title compound (0.28 g, 99%) as a colorless solid. [α]D25=2.28 (c 1.05, DMSO).
99% With triethylamine; trifluoroacetic acid In dichloromethane at 20℃; for 1h; 34.34c (34c)5-Chloro-2-fluoro-4-[(lS,2R)-2-(l-methyl-lH-pyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide Toa solution of the 5-chloro-N-(2,4-dimethoxyben-zyl)-2-fluoro-4-[(lS,2R)-2-(l-methyl-lH-pyrazol-5-yl)cy-clohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide(0.371 g, 0.602 mmol) prepared in Example 34b and triethylsilane (0.48 mL, 3.01 mmol) in dichloromethane (6.0mL), trifluoroacetic acid (0.60 mL) was added at room temperature, and thereaction solution was stirred for 1 hour. The reaction solution wasconcentrated, and the residue was purified with silica gel chromatography(ethyl acetate/metha-nol=6:l) to yield the title compound (0.28 g, 99%) as acolorless solid.
99% With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 1h;
81.6% With hydrogenchloride; triphenylphosphine In water; toluene; acetonitrile at 20 - 40℃; for 3.08333h; 1-4 1-4) 5-Chloro-2-fluoro-4-{ [(1 S,2R)-2-(i -methyl-i Hpyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzenesulfonamide (Step of Removing 2,4-dime- thoxybenzyl Group) To a mixture of the solution of 5-chioro-N-(2,4- dimethoxybenzyl)-2-fluoro-4-{ [(1 S,2R)-2-(i -methyl- iHpyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzene- sulfonamide in toluene obtained in Example 1-3), acetonitrile (360 mE), and triphenylphosphine (17.46 g, 0.067 mol), 35% hydrochloric acid (34.68 g) was added dropwise at an internal temperature in the range of 20° C. to 30° C. over approximately 5 minutes. After the completion of dropwise addition, the mixture was stirred at an internal temperature of approximately 40° C. for approximately 3 hours. The reaction solution was cooled to approximately 25° C. Water (120 mE) and toluene (300 mE) were added thereto, and the mixture was stirred for approximately 10 minutes. After separation into an organic layer and an aqueous layer, acetonitrile (240 mE) and toluene (240 mE) were added to the aqueous layer, and the aqueous layer was washed. This operation was repeated twice. To the aqueous layer thus washed, activated carbon (1 .8 g) was added, and the mixture was stirred for approximately 30 minutes. Then, activated carbon was filtered oil and washed. The aqueous layer thus treated with activated carbon was concentrated under reduced pressure until the amount of the solution became approximately 240 mE.10293] The concentrate was cooled to an internal temperature of approximately 25° C. Then, ethanol (240 mE) was added thereto, and the pH was adjusted to approximately 1.3 with a 2 N aqueous sodium hydroxide solution. Then, the internal temperature was elevated to approximately 40° C. Seed crystals of 5-chloro-2-fluoro-4-{ [(1 S,2R)-2-(i -methyl1 H-pyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)ben- zenesulfonamide (12 mg) were added thereto, and the mixture was stirred for approximately 2 hours. The internal temperature was lowered to approximately 25° C. Then, the pH was adjusted to approximately 4.0 with a 2 N aqueous sodium hydroxide solution. Afier stirring overnight, crystals were collected by filtration, washed, and then dried to obtain crystals of 5-chloro-2-fluoro-4-{ [(1 S,2R)-2-(i -methyl-i Hpyrazol-5-yl)cyclohexyl]oxy}-N-(pyrimidin-4-yl)benzene- sulfonamide (25.32 g, yield: 81.6%).

  • 3
  • [ 286-20-4 ]
  • [ 1450595-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C 1.2: 20 h / -78 °C 2.1: ethanol; hexane / Resolution of racemate 3.1: sodium hydride / 1 h / 0 - 20 °C / Inert atmosphere 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h / 20 °C
  • 4
  • [ 1354787-43-1 ]
  • [ 1450595-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate / tetrahydrofuran; N,N-dimethyl acetamide / 1.25 h / -20 - -10 °C 2: triphenylphosphine; hydrogenchloride / water; acetonitrile; toluene / 3.08 h / 20 - 40 °C
  • 5
  • (1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclohexan-1-ol [ No CAS ]
  • [ 1450595-86-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol; hexane / Resolution of racemate 2: sodium hydride / 1 h / 0 - 20 °C / Inert atmosphere 3: trifluoroacetic acid; triethylsilane / dichloromethane / 1 h / 20 °C
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