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[ CAS No. 146093-46-1 ] {[proInfo.proName]}

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Chemical Structure| 146093-46-1
Chemical Structure| 146093-46-1
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Product Details of [ 146093-46-1 ]

CAS No. :146093-46-1 MDL No. :MFCD04038459
Formula : C12H24N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LBQDLHPFISVBRU-UHFFFAOYSA-N
M.W :228.33 Pubchem ID :1514258
Synonyms :

Calculated chemistry of [ 146093-46-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 68.91
TPSA : 55.56 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) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.6
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 1.07
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.73
Solubility : 4.29 mg/ml ; 0.0188 mol/l
Class : Very soluble
Log S (Ali) : -2.04
Solubility : 2.1 mg/ml ; 0.00921 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.73
Solubility : 4.23 mg/ml ; 0.0185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.21

Safety of [ 146093-46-1 ]

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 [ 146093-46-1 ]

* 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 [ 146093-46-1 ]
  • Downstream synthetic route of [ 146093-46-1 ]

[ 146093-46-1 ] Synthesis Path-Upstream   1~12

  • 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
  • [ 150022-51-8 ]
  • [ 146093-46-1 ]
YieldReaction ConditionsOperation in experiment
78% at 20℃; for 5.5 h; 5.5 g (15.34 mmol) of tert-butyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethyl)piperidine-1-carboxylate prepared previously are solubilized in 40 ml of ethanol amine and the mixture is stirred at room temperature for 5.5 h.
Then it is poured into 150 ml of water and extracted twice with 200 ml of dichloromethane.
The organic phases are dried on MgSO4, filtered and evaporated, and 2.74 g (11.95 mmol) of tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate are obtained in the form of a clear oil after purification by flash chromatography on silica gel (eluent: dichloromethane/methanol/NH4OH=90/9/1percent) Yield: 78percent
1H NMR (CDCl3) δ: 1.10 (m, 2H); 1.40 (m, 2H); 1.45 (s, 9H); 1.49 (Is; 3H); 1.64 (m, 2H); 3.58 (m, 4H); 4.07 (m, 2H).
24.7 g With hydrazine hydrate In ethanol at 50 - 60℃; for 22 h; To the tert-butyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethyl)piperidine-1-carboxylate (245 g) in ethanol ( 2 L) was added hydrazine hydrate (55 mL, ~1 mol) in one portion and the mixture heated to 50-60 °C for 22 hours. The resulting slurry was cooled to 30 °C, filtered and washed with ethanol (800 mL). The filtrate was evaporated, taken up in CH2Cl2 (1.3 L) and re-filtered through a pad of Celite, washing with CH2Cl2 (700 mL). This filtrate was washed with 1M sodium hydroxide (1 L), dried (MgSO4) and evaporated to afford the tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (137.8 g) as a hazy yellow oil. The sodium hydroxide layer from above was passed through the solids along with additional CH2Cl2 (400 mL). The layers were separated and the organics dried (MgSO4) and evaporated to afford the amine (24.7 g) as a hazy colorless oil. To the tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate (228.6 g, 1.0 mol) in CH2Cl2 (2 L) at 4 °C was added pyridine (310 mL, 3.8 mol) followed by 2-nitrobenzenesulfonyl chloride (278 g, 1.25 mol) in portions. The mixture was stirred at room temperature overnight then quenched by addition of 2M NaH2PO4 (1.4 L). The layers were separated and the aqueous (pH ~5) re-extracted with CH2Cl2 (500 mL) then EtOAc (500 mL). The combined organics were dried (MgSO4) and filtered through a pad of silica (220 g), washing with 20percent EtOAc in CH2Cl2 (650 mL). The filtrate was evaporated and azeotroped with toluene to afford crude sulfonamide (400 g). Chromatography (1 kg silica, eluent 2-10percent EtOAc inn CH2Cl2) afforded sulfonamide (293.3 g) as a yellow solid. 1H NMR (500 MHz, CDCl3) d 8.14 (m, 1H), 7.87 (m, 1H), 7.78-7.74 (m, 2H), 5.22 (t, J = 5.9 Hz, 1H), 4.06 (br s, 2H), 3.14 (m, 2H), 2.16 (br s, 2H), 1.61-1.39 (m, 5H), 1.44 (s, 9H), 1.06 (m, 2H).
Reference: [1] Patent: US2015/336943, 2015, A1, . Location in patent: Paragraph 1414-1416
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811
  • 3
  • [ 146093-45-0 ]
  • [ 146093-46-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
  • 4
  • [ 89151-44-0 ]
  • [ 146093-46-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
[3] Patent: US2015/336943, 2015, A1,
  • 5
  • [ 79099-07-3 ]
  • [ 146093-46-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
[2] Patent: WO2015/138895, 2015, A1,
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811
  • 6
  • [ 622-26-4 ]
  • [ 146093-46-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
  • 7
  • [ 24424-99-5 ]
  • [ 146093-46-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
  • 8
  • [ 89151-46-2 ]
  • [ 146093-46-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1779 - 1788
  • 9
  • [ 147699-19-2 ]
  • [ 146093-46-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811
  • 10
  • [ 135716-08-4 ]
  • [ 146093-46-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
  • 11
  • [ 135716-09-5 ]
  • [ 146093-46-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2167 - 2172
  • 12
  • [ 146093-46-1 ]
  • [ 896103-62-1 ]
Reference: [1] Patent: US2014/171403, 2014, A1, . Location in patent: Page/Page column
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