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[ CAS No. 256411-39-9 ] {[proInfo.proName]}

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Chemical Structure| 256411-39-9
Chemical Structure| 256411-39-9
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Product Details of [ 256411-39-9 ]

CAS No. :256411-39-9 MDL No. :MFCD09801019
Formula : C12H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LARQASBBVGBMDA-UHFFFAOYSA-N
M.W : 224.30 Pubchem ID :22248390
Synonyms :

Calculated chemistry of [ 256411-39-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.96
TPSA : 53.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.61
Log Po/w (XLOGP3) : 1.55
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.33
Log Po/w (SILICOS-IT) : 1.44
Consensus Log Po/w : 1.82

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.94
Solubility : 2.56 mg/ml ; 0.0114 mol/l
Class : Very soluble
Log S (Ali) : -2.28
Solubility : 1.18 mg/ml ; 0.00525 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.77
Solubility : 3.79 mg/ml ; 0.0169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 256411-39-9 ]

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 [ 256411-39-9 ]

* 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 [ 256411-39-9 ]
  • Downstream synthetic route of [ 256411-39-9 ]

[ 256411-39-9 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 256411-39-9 ]
  • [ 146093-46-1 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium hydroxide; hydrogen In methanol at 50℃; for 5 h; A mixture of tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (20 g, 89.29 mmol) and NH4OH (9 mL) in MeOH (200 mL) was hydrogenated with Raney Ni (6 g, 101.69 mmol) at 50 °C for 5 h under 50 psi of H2. The mixture was filtered through a celite pad and the filtrate was concentrated to afford product (20.5 g, 100percent) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.06 - 1.19 (m, 2H) 1.44 (d, J=7.41 Hz, 2H) 1.47 (s, 9H) 1.50 - 1.58 (m, 1H) 1.66 (d, J=12.49 Hz, 2H) 2.09 (br. s., 2H) 2.70 (t, J=12.29 Hz, 2H) 2.75 - 2.83 (m, 2H) 4.08 (br. s., 2H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811
  • 2
  • [ 773837-37-9 ]
  • [ 123855-51-6 ]
  • [ 256411-39-9 ]
YieldReaction ConditionsOperation in experiment
76.6% at 20 - 80℃; for 24 h; NaCN (4.00 g, 80.0 mmol) and H2O (20 ml) at room temperature were added to a stirred solution of tert-butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (15.3 g) in EtOH (80 ml). The reaction mixture was stirred at 80 °C for 24 h. After completing the reaction, the solvents were concentrated in vacuo. The residue was dissolved in AcOEt (300 ml) and H2O (100 ml). The aqueous layer was extracted with AcOEt (300 ml). The combined organic layers were washed with brine (100 ml), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane-AcOEt) to give 7 (6.87 g, 76.6percent from 7) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.21-1.31 (2H, m), 1.46 (9H, s), 1.78-1.86 (3H, m), 2.31 (2H, d, J = 6.4 Hz), 2.64-2.78 (2H, m), 4.07-4.21 (2H, m).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3249 - 3253
  • 3
  • [ 782493-57-6 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: WO2004/92124, 2004, A2, . Location in patent: Page 91
[2] Patent: US2007/238723, 2007, A1, . Location in patent: Page/Page column 46
  • 4
  • [ 142374-19-4 ]
  • [ 256411-39-9 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9334 - 9337,4
[2] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9334 - 9337
  • 5
  • [ 151-50-8 ]
  • [ 123855-51-6 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: US2005/107434, 2005, A1, . Location in patent: Page/Page column 17
  • 6
  • [ 773837-37-9 ]
  • [ 161975-39-9 ]
  • [ 256411-39-9 ]
YieldReaction ConditionsOperation in experiment
6.87 g at 80℃; for 24 h; 4-(cyanomethyl)piperidine-1-carboxylate
tert-Butyl 4-[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (15.3 g) was dissolved in ethanol (80 mL), water (20 mL) and sodium cyanide (4.0 g, 80 mmol) were added, and stirring was conducted at 80° C. for 24 hours.
Ethanol was distilled off, water and ethyl acetate were added, and then the resultant mixture was subject to Celite filtration, followed by extraction with ethyl acetate.
The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by using silica gel column chromatography (hexane:ethyl acetate=3:1→2:1) to give tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (6.87 g, 77percent, 3 steps) as a white solid.
1H-NMR (CDCl3) δ: 1.21-1.31 (2H, m), 1.46 (9H, s), 1.78-1.86 (3H, m), 2.31 (2H, d, J=6.4 Hz), 2.64-2.78 (2H, m), 4.07-4.21 (2H, m).
Reference: [1] Patent: US2013/102621, 2013, A1, . Location in patent: Paragraph 0281; 0282
  • 7
  • [ 773837-37-9 ]
  • [ 166815-96-9 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: US2017/29430, 2017, A1, . Location in patent: Paragraph 0257
  • 8
  • [ 79099-07-3 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: WO2011/104680, 2011, A1,
[2] Patent: US2012/220609, 2012, A1,
[3] Patent: WO2015/22663, 2015, A1,
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811
[5] Patent: US2011/112103, 2011, A1,
  • 9
  • [ 161975-39-9 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: WO2004/54973, 2004, A2, . Location in patent: Page 38
  • 10
  • [ 41979-39-9 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: WO2011/104680, 2011, A1,
  • 11
  • [ 4248-19-5 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: WO2011/104680, 2011, A1,
  • 12
  • [ 6457-49-4 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: US2013/102621, 2013, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3249 - 3253
  • 13
  • [ 24424-99-5 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: US2013/102621, 2013, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3249 - 3253
  • 14
  • [ 123855-51-6 ]
  • [ 256411-39-9 ]
Reference: [1] Patent: US2013/102621, 2013, A1,
[2] Patent: US2017/29430, 2017, A1,
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