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[ CAS No. 90729-43-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 90729-43-4
Chemical Structure| 90729-43-4
Structure of 90729-43-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 90729-43-4 ]

CAS No. :90729-43-4 MDL No. :MFCD00865661
Formula : C32H39NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MJJALKDDGIKVBE-UHFFFAOYSA-N
M.W : 469.66 Pubchem ID :3191
Synonyms :
LAS-W 090;RP64305;Kestin;Evastel;Busidril;Bactil;Ebatrol;Aleva;Ebastel;Kestine;Brand name: Evastin

Calculated chemistry of [ 90729-43-4 ]

Physicochemical Properties

Num. heavy atoms : 35
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.41
Num. rotatable bonds : 10
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 149.12
TPSA : 29.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.01
Log Po/w (XLOGP3) : 7.2
Log Po/w (WLOGP) : 6.51
Log Po/w (MLOGP) : 4.73
Log Po/w (SILICOS-IT) : 7.33
Consensus Log Po/w : 6.16

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -7.01
Solubility : 0.0000461 mg/ml ; 0.0000000981 mol/l
Class : Poorly soluble
Log S (Ali) : -7.64
Solubility : 0.0000107 mg/ml ; 0.0000000228 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.94
Solubility : 0.0000000537 mg/ml ; 0.0000000001 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.16

Safety of [ 90729-43-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P273-P301+P312-P330 UN#:N/A
Hazard Statements:H302-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 90729-43-4 ]

* 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 [ 90729-43-4 ]
  • Downstream synthetic route of [ 90729-43-4 ]

[ 90729-43-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 1338066-81-1 ]
  • [ 43076-61-5 ]
  • [ 90729-43-4 ]
YieldReaction ConditionsOperation in experiment
55.27% With potassium carbonate In 4-methyl-2-pentanone at 105 - 116℃; for 2.25 h; Inert atmosphere 2.2 Synthesis of I" from Benzyhydryloxypiperidine toluenesulfonate Benzhydryloxypiperidine toluenesulfonate (1 1.44 g, 0.025 mol), 4'-tert-butyl-4- chlorobutyrophenone (10.15 g, 170 mol percent), potassium carbonate (8.47 g, 245 mol percent) and methyl isobutyl ketone (18.3 g) were placed in a round bottom flask and a further 20 mL of methyl isobutyl ketone were added and the reaction mixture was placed under a nitrogen atmosphere. The mixture was heated to between 1 15-116°C and vigorous evolution of gas was noted. The reaction mixture was heated at reflux temperature (105-1 15 °C) for 2 h and 15 minutes and then cooled to 30 °C internal temperature. Water (50 mL) was added and the phases were separated. The organic phase was washed with water (3x 50 mL) and then concentrated under reduced pressure (45 °C, 8 mbar) to give the crude product. The crude material was suspended in ethanol (30 mL, 96percent denatured with toluene) and the mixture was heated to reflux (82°C). The resulting solution was stirred at reflux temperature for 15 minutes and then cooled to 30 °C (the solution was seeded with a small quantity of I") and stirred at 30 °C for 30 minutes. The resulting suspension was then cooled to 2-3 °C and stirred at this temperature for 1 h. The product was isolated by filtration and washed with ethanol (3 x 5 niL). The moist product was dried in a vacuum oven (45°C) to give pure I" (6.49 g, 55.27percent). HPLC purity (areapercent): 99.27percent RRT 0.62 0.38percent.
55.27% With potassium carbonate In 4-methyl-2-pentanone at 105 - 116℃; Inert atmosphere 2.2
Synthesis of I' from Benzyhydryloxypiperidine toluenesulfonate
Benzhydryloxypiperidine toluenesulfonate (11.44 g, 0.025 mol), 4'-tert-butyl-4-chlorobutyrophenone (10.15 g, 170 mol percent), potassium carbonate (8.47 g, 245 mol percent) and methyl isobutyl ketone (18.3 g) were placed in a round bottom flask and a further 20 mL of methyl isobutyl ketone were added and the reaction mixture was placed under a nitrogen atmosphere.
The mixture was heated to between 115-116°C and vigorous evolution of gas was noted.
The reaction mixture was heated at reflux temperature (105-115 °C) for 2 h and 15 minutes and then cooled to 30 °C internal temperature.
Water (50 mL) was added and the phases were separated.
The organic phase was washed with water (3x 50 mL) and then concentrated under reduced pressure (45 °C, 8 mbar) to give the crude product.
The crude material was suspended in ethanol (30 mL, 96percent denatured with toluene) and the mixture was heated to reflux (82°C).
The resulting solution was stirred at reflux temperature for 15 minutes and then cooled to 30 °C (the solution was seeded with a small quantity of I') and stirred at 30 °C for 30 minutes.
The resulting suspension was then cooled to 2-3°C and stirred at this temperature for 1 h.
The product was isolated by filtration and washed with ethanol (3 x 5 mL).
The moist product was dried in a vacuum oven (45°C) to give pure I' (6.49 g, 55.27percent). HPLC purity (areapercent): 99.27percent RRT 0.62 0.38percent.
Reference: [1] Patent: WO2011/121099, 2011, A2, . Location in patent: Page/Page column 39-40
[2] Patent: EP2371817, 2011, A1, . Location in patent: Page/Page column 27
  • 2
  • [ 65214-86-0 ]
  • [ 43076-61-5 ]
  • [ 90729-43-4 ]
Reference: [1] Patent: WO2011/121099, 2011, A2, . Location in patent: Page/Page column 42
  • 3
  • [ 43076-61-5 ]
  • [ 90729-43-4 ]
Reference: [1] Patent: EP2371817, 2011, A1, . Location in patent: Page/Page column 29
  • 4
  • [ 58258-01-8 ]
  • [ 43076-61-5 ]
  • [ 90729-43-4 ]
YieldReaction ConditionsOperation in experiment
66.43% With sodium hydrogencarbonate In toluene for 12 h; Reflux Example 3. Preparation of discoloured l-[4-(l,l-dimethyIethyl)phenyI]-4-[4- (diphenylmethoxy)-l-piperidinyl]-l-butanone I"A toluene solution of 4-benzhydryloxypiperidine (73.27 g of the toluene solution contained 26.74 g of 4-benzhydryloxypiperidine), sodium hydrogen carbonate (14.28 g), DMF (5.3 mL) and 4'-tert-butyl-4-chloro-butyrophenone (28.65 g) were heated to reflux temperature. The reaction mixture was heated at reflux temperature for 12 h, to produce a solution of I" of 84.3percent) purity on the basis of HPLC area-percent and then cooled to room temperature. The orange reaction mixture was washed with water (3 x 100 mL) and the organic phase wasconcentrated under reduced pressure. Ethanol (110 mL) was added to the residue and the mixture was heated to reflux. The hot solution was filtered and the filtrate was cooled to 2 °C. The product was isolated by filtration and washed with ethanol (5 x 20 mL). The product was dried in a vacuum oven for several hours to afford the title compound (31.2 g, 66.43 percent) as a beige solid (commercial I" is white and specifications (such as those found in the European Pharmacopoeia) require a white to almost white crystalline substance). HPLC purity 99.77 percent, significant impurities at relative retention times 0.05 and 0.19 were observed and had HPLC area-percent of 0.04 and 0.06percent>. Discolouration was also sometimes observed when other solvents, including methyl isobutyl ketone were used, but was able to be efficiently suppressed when air was excluded from the reaction mixture, or was able to be efficiently suppressed when an adequate purification procedure by salt formation/neutralization, alternatively or optionally in combination with recrystallization, was used.
Reference: [1] Patent: WO2011/121099, 2011, A2, . Location in patent: Page/Page column 40-41
[2] Patent: EP2371817, 2011, A1, . Location in patent: Page/Page column 28
  • 5
  • [ 1338066-82-2 ]
  • [ 90729-43-4 ]
Reference: [1] Patent: WO2011/121099, 2011, A2, . Location in patent: Page/Page column 49
  • 6
  • [ 5382-16-1 ]
  • [ 90729-43-4 ]
Reference: [1] Patent: WO2012/76919, 2012, A1,
  • 7
  • [ 43076-61-5 ]
  • [ 90729-43-4 ]
Reference: [1] Patent: WO2012/76919, 2012, A1,
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