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[ CAS No. 118292-40-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 118292-40-3
Chemical Structure| 118292-40-3
Structure of 118292-40-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 118292-40-3 ]

CAS No. :118292-40-3 MDL No. :MFCD00867628
Formula : C21H21NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :OGQICQVSFDPSEI-UHFFFAOYSA-N
M.W : 351.46 Pubchem ID :5381
Synonyms :
AGN 190168
Chemical Name :Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate

Calculated chemistry of [ 118292-40-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 101.62
TPSA : 64.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.04
Log Po/w (XLOGP3) : 4.9
Log Po/w (WLOGP) : 4.51
Log Po/w (MLOGP) : 4.0
Log Po/w (SILICOS-IT) : 5.6
Consensus Log Po/w : 4.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.26
Solubility : 0.00192 mg/ml ; 0.00000545 mol/l
Class : Moderately soluble
Log S (Ali) : -5.99
Solubility : 0.000359 mg/ml ; 0.00000102 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.77
Solubility : 0.0000598 mg/ml ; 0.00000017 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.39

Safety of [ 118292-40-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 118292-40-3 ]

* 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 [ 118292-40-3 ]
  • Downstream synthetic route of [ 118292-40-3 ]

[ 118292-40-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 118292-06-1 ]
  • [ 49608-01-7 ]
  • [ 118292-40-3 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With potassium carbonate; triphenylphosphine In toluene at 45 - 50℃;
Stage #2: at 45 - 115℃;
Charged ethyl 6-chloronicotinate (10.0 gm) in a R.B. Flask arranged with reflux condenser on oil bath, containing toluene (100 ml). Stirred and charged potassium carbonate (30.0 gm), triphenylphosphine (4.0 gm) and 5percent Pd/C (4.0 gm) to the reaction solution. Gradually raised the temperature to 45-50 C and maintained under stirring at 45 - 50°C for 2 hours. Charged 6-ethynyl-4,4-dimethylthiochromane (8 gm) and Copper iodide (0.05 gm) at 45-50°C. After charging, the reaction temperature was raised to 105- 115°C and maintained under stirring at 105-1150C temperature for 10 hours. After completion, the reaction mass was cooled to 25-300C and filtered the catalyst Pd/C. To the filtrate charged water (300 ml) and stirred for 30 min. Separated the organic layer and the aqueous layer was extracted with toluene (100 ml). Separated the organic layer and combined all organic layers. Concentrated the solvent under reduced pressure to get residual mass. Charged hexane (25 ml) to the residual mass and stirred at 25-300C for 1.0 hour. Cooled the reaction to -10 to 5°C and maintained for 1.0 hour. Filtered the solid Tazarotene and dried in oven till constant weight. Weight of Tazarotene = 8.3 gm percent Yield = 60.0 percent.
9 g
Stage #1: With palladium on activated charcoal; potassium carbonate; sodium sulfate; triphenylphosphine In toluene at 50 - 55℃; for 2 h; Inert atmosphere
Stage #2: With copper(l) iodide In toluene at 105 - 115℃;
To 188 ml of toluene was added palladium on carbon (10 g) under N2 atmosphere. The mixture was heated to 105-115 °C to remove water by azeotropic distillation. Thereaction mass was cooled to 50-55 °C. To the above mixture, anhydrous sodium sulphate(12.5 g), anhydrous potassium carbonate (37.5 g), triphenylphosphine (5 g), ethyl 6-chioronicotinoate (12.5 g) and toluene (12.5 ml) were added at 50-55 °C and stirred for 2hours. To the above mixture, 4,4-dimethyl-6-ethynylthiochroman (10 g), cuprous iodide(0.06 g) and toluene (12.5 ml) were added and the reaction mixture was heated to 105-115 °C for 10-12 hours. The reaction mixture was cooled to 25-30 °C and water (125 ml)was added. The biphasi reaction mixture was filtered and from the filtrate, product enriched organic layer was separated. The organic layer was washed with water (2 X 65. ml) and brine solution (2 X 65 ml), dried over anhydrous sodium sulphate (5 g) and all the solvent was distilled off to get residual mass. The residual mass was dissolved in n20 heptane (50 ml) at 75-80 °C, which was treated with activated charcoal, neutral aluminaand filtered. The filtrate was stirred at 25-30 °C for 20 hours. The resulted solid was filtered off, washed with n-heptane (12.5 ml) and dried to yield 9 g of tazarotene. (HPLC purity of tazarotene— 97.64percent; Content of dimer impurity - 1.31percent).
Reference: [1] Patent: WO2009/116075, 2009, A2, . Location in patent: Page/Page column 12
[2] Patent: WO2015/107542, 2015, A2, . Location in patent: Page/Page column 12
[3] Patent: WO2015/107542, 2015, A3, . Location in patent: Page/Page column 12
  • 2
  • [ 118292-06-1 ]
  • [ 118292-40-3 ]
Reference: [1] Patent: US5602130, 1997, A,
[2] Patent: US5089509, 1992, A,
  • 3
  • [ 118292-06-1 ]
  • [ 118292-40-3 ]
Reference: [1] Patent: WO2006/59345, 2006, A2, . Location in patent: Page/Page column 20-21
[2] Patent: WO2006/59345, 2006, A2, . Location in patent: Page/Page column 22
  • 4
  • [ 64-17-5 ]
  • [ 118292-41-4 ]
  • [ 118292-40-3 ]
Reference: [1] Patent: US2007/238881, 2007, A1, . Location in patent: Page/Page column 6
  • 5
  • [ 118292-06-1 ]
  • [ 49608-01-7 ]
  • [ 118292-40-3 ]
Reference: [1] Patent: US5089509, 1992, A,
  • 6
  • [ 78-39-7 ]
  • [ 118292-41-4 ]
  • [ 118292-40-3 ]
Reference: [1] Patent: US2007/238881, 2007, A1, . Location in patent: Page/Page column 7
  • 7
  • [ 952294-18-7 ]
  • [ 78-39-7 ]
  • [ 118292-40-3 ]
Reference: [1] Patent: US2007/238881, 2007, A1, . Location in patent: Page/Page column 7
  • 8
  • [ 112110-44-8 ]
  • [ 118292-40-3 ]
Reference: [1] Organic Process Research and Development, 2005, vol. 9, # 5, p. 646 - 650
[2] Organic Process Research and Development, 2005, vol. 9, # 5, p. 646 - 650
  • 9
  • [ 864841-54-3 ]
  • [ 118292-40-3 ]
Reference: [1] Organic Process Research and Development, 2005, vol. 9, # 5, p. 646 - 650
[2] Organic Process Research and Development, 2005, vol. 9, # 5, p. 646 - 650
  • 10
  • [ 864841-55-4 ]
  • [ 118292-40-3 ]
Reference: [1] Organic Process Research and Development, 2005, vol. 9, # 5, p. 646 - 650
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