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[ CAS No. 167263-04-9 ] {[proInfo.proName]}

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Chemical Structure| 167263-04-9
Chemical Structure| 167263-04-9
Structure of 167263-04-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 167263-04-9 ]

CAS No. :167263-04-9 MDL No. :MFCD11227109
Formula : C16H21N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OUILGYJQVAMETA-UHFFFAOYSA-N
M.W : 287.36 Pubchem ID :53439111
Synonyms :

Calculated chemistry of [ 167263-04-9 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 83.31
TPSA : 66.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.81
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.68
Solubility : 0.595 mg/ml ; 0.00207 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.478 mg/ml ; 0.00167 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.055 mg/ml ; 0.000191 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.39

Safety of [ 167263-04-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 167263-04-9 ]

* 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 [ 167263-04-9 ]
  • Downstream synthetic route of [ 167263-04-9 ]

[ 167263-04-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 2739-97-1 ]
  • [ 118753-70-1 ]
  • [ 167263-04-9 ]
YieldReaction ConditionsOperation in experiment
44% With sodium hydride In DMF (N,N-dimethyl-formamide); oil at 0 - 60℃; for 5.63333 h; Sodium hydride (60percent in mineral oil, 2.04g, 51mmol) was added portion wise over 8 minutes to a stirring solution of 2-pyridineacetonitrile (1. 8ml, 17mmol) and N- (tert-butyloxycarbonyl) bis (2-chloroethyl) amine in anhydrous DMF (50ml) at 0OC. The reaction was then heated at 60°C for 5 1/2hours. The reaction was cooled and extracted into ethyl acetate (4 x 150ml), and washed with water (3 x 200ml). The organic layer was then dried over anhydrous MgSO.cents., filtered and evaporated in vacuo to give a red/black oil. This was absorbed onto silica and purified by column chromatography using 20percent ethyl acetate in isohexane to give ter-butyl 4-cyano-4-pyridin-2-ylpiperidine-1-carboxylate as an orange solid (2.13g, 44percent). 1H NMR 8 (ppm) 360MHz (CDC13): 1.48 (9 H, s), 2.04-2. 08 (2 H, m), 2.17-2. 25 (2 H, m), 3.15-3. 28 (2 H, m), 4.20-4. 35 (2 H, m), 7.25-7. 29 (1 H, m), 7.61 (1 H, d, J = 8Hz), 7.73-7. 78 (1 H, m), 8. 61 (1 H, dd, J = 0.7, 3.9Hz). MSp m/z for MH+ = 287 (- 56).
Reference: [1] Patent: WO2005/51390, 2005, A1, . Location in patent: Page/Page column 28
[2] Bioorganic and medicinal chemistry letters, 2000, vol. 10, # 15, p. 1625 - 1628
[3] Patent: US5635510, 1997, A,
[4] Patent: US5824690, 1998, A,
  • 2
  • [ 372-48-5 ]
  • [ 91419-52-2 ]
  • [ 167263-04-9 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 46, p. 6303 - 6306
[2] Patent: WO2007/41025, 2007, A2, . Location in patent: Page/Page column 19
[3] Patent: WO2009/51715, 2009, A1, . Location in patent: Page/Page column 25-26
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1488 - 1491
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1492 - 1495
[6] Patent: US2007/254880, 2007, A1, . Location in patent: Page/Page column 15; 17
[7] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4773 - 4780
[8] Patent: WO2011/84371, 2011, A1, . Location in patent: Page/Page column 33-34
[9] Patent: WO2012/158475, 2012, A1, . Location in patent: Page/Page column 41
  • 3
  • [ 372-48-5 ]
  • [ 167263-04-9 ]
YieldReaction ConditionsOperation in experiment
4 g With lithium hexamethyldisilazane In tetrahydrofuran at 18 - 25℃; for 1.5 h; To a solution of 1-(tert-butoxycarbonyl)-4-cyano-2,3,4,5-tetrahydropyridin-1-ium (3.24 g, 15.43 mmol) and2-fluoropyridine (1.65 g, 16.97 mmol) in THF (20 mL) at RTwas added LHMDS (18.5 mL, 18.5 mmol, 1 M in THFsolution). The reaction mixture was stirred at RT for 1.5 h.Upon completion of the reaction, the reaction mixture wasquenched with water (50 mL) and extracted with EtOAc (50mLx3). The combined organic phase was dried over anhydrousNa2S04 and concentrated under reduced pressure. Theresidue was purified by silica-gel column chromatography toafford 4 g of tert-butyl 4-cyano-4-(pyridin-2-yl)piperidine-1-carboxylate. LC-MS (ESI+): m/z 288 [M+Ht.
Reference: [1] Patent: US2018/258065, 2018, A1, . Location in patent: Paragraph 0129; 0191
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