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[ CAS No. 91419-53-3 ] {[proInfo.proName]}

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Chemical Structure| 91419-53-3
Chemical Structure| 91419-53-3
Structure of 91419-53-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 91419-53-3 ]

CAS No. :91419-53-3 MDL No. :MFCD01861222
Formula : C11H18N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UEFZTXGFHKPSFS-UHFFFAOYSA-N
M.W : 210.27 Pubchem ID :2756785
Synonyms :

Calculated chemistry of [ 91419-53-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.82
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.15
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) : -6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 1.32
Log Po/w (WLOGP) : 1.78
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 1.06
Consensus Log Po/w : 1.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.78
Solubility : 3.51 mg/ml ; 0.0167 mol/l
Class : Very soluble
Log S (Ali) : -2.04
Solubility : 1.91 mg/ml ; 0.0091 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.37
Solubility : 9.05 mg/ml ; 0.0431 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.74

Safety of [ 91419-53-3 ]

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 [ 91419-53-3 ]

* 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 [ 91419-53-3 ]
  • Downstream synthetic route of [ 91419-53-3 ]

[ 91419-53-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 91419-49-7 ]
  • [ 91419-53-3 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 20℃; 3(B)
3-Cyano-piperidine-1-carboxylic acid tert-butyl ester
Phosphorus oxychloride (0.64 mL, 6.89 mmol) was added dropwise at 0° C. to a solution of 3-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester (1.58 g, 6.89 mmol) in pyridine (15 mL), under nitrogen atmosphere.
After stirring overnight at room temperature, ethyl acetate was added and the solution was washed with 10percent HCl (2 times).
The phases were separated and the organics were dried over sodium sulphate and evaporated to dryness under reduced pressure.
The title compound was used for the next step without further purification.
Yield: quantitative; LCMS (RT): 4.48 min (Method A); MS (ES+) gave m/z: 211.1.
100% With phosphorus pentoxide In pyridine at 0 - 20℃; Phosphorus oxychloride (0.64 mL, 6.89 mmol) was added dropwise at 0°C to a solution of S-carbamoyl-piperidine-l-carboxylic acid tert-butyl ester (1.58 g, 6.89 mmol) in pyridine (15 mL), under nitrogen atmosphere. After stirring overnight at room temperature, ethyl acetate was added and the solution was washed with 10percent HCl (2 times). The phases were separated and the organics were dried over sodium sulphate and evaporated to dryness under reduced pressure. The title compound was used for the next step without further purification. Yield: quantitative; LCMS (RT): 4.48 min (Method A); MS (ES+) gave m/z: 211.1 (MH+).
87% With triethylamine; trifluoroacetic anhydride In dichloromethane at 20℃; for 16 h; Tert-butyl 3-cyanopiperidine-l-carboxylate (3). To a solution of tert-butyl-3- carbamoyl piperidine-l-carboxylate 2 (1.0 g, 4 mmol) in anhydrous dichloromethane (20 mL), triethylamine (3.1 g, 31.0 mmol) was added followed by the dropwise addition of trifluoroaceticanhydride (4.1 g, 20.0 mmol). The resulting mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was partitioned between dichloromethane (50 mL) and water (50 mL). The organic phase was washed with saturated bicarbonate solution (100 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 3 (800 mg, 87percent) as a thick liquid. 1H NMR (400 MHz, CDC13) δ 1.49 (s, 9H), 1.77 (m, 2H), 1.97 (brs, 1H), 2.66 (m, 1H), 3.35-3.84 (brs, 4H),
53%
Stage #1: at 0℃; for 1 h;
Stage #2: With sodium hydrogencarbonate In water
Step 3. Tert-butyl 3-cyanopiperidine-1-carboxylate; A 250-mL 3-necked round-bottomed flask was charged with a solution of tert-butyl 3-carbamoylpiperidine-1-carboxylate (5 g, 21.49 mmol, 1.00 equiv, 98percent) in pyridine (50 mL). To this solution, POCl3 (5 g, 32.24 mmol, 1.50 equiv, 98percent) was added drop wise at 0° C. and allowed to stir at 0° C. for 1 hour. The progress was monitored by TLC (EA:PE=1:1). The pyridine was removed by distillation. The mixture was diluted with H2O (40 mL) and pH was adjusted to 8 by addition of aqueous NaHCO3. Then, the resulting mixture was extracted with ethyl acetate (3.x.30 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The crude was purified by distillation under reduced pressure (30 mm Hg) and the fractions collected at 40° C. to afford tert-butyl 3-cyanopiperidine-1-carboxylate as yellow oil (2.6 g, 53percent).

Reference: [1] Patent: US2009/215822, 2009, A1, . Location in patent: Page/Page column 11
[2] Patent: WO2006/123257, 2006, A2, . Location in patent: Page/Page column 34
[3] Journal of the American Chemical Society, 2018, vol. 140, # 5, p. 1627 - 1631
[4] Tetrahedron, 2002, vol. 58, # 18, p. 3561 - 3577
[5] Patent: WO2014/149164, 2014, A1, . Location in patent: Paragraph 00606
[6] Patent: US8080566, 2011, B1, . Location in patent: Page/Page column 38
[7] European Journal of Medicinal Chemistry, 1984, vol. 19, # 2, p. 181 - 186
[8] Tetrahedron Letters, 1997, vol. 38, # 12, p. 2099 - 2102
[9] Journal of Medicinal Chemistry, 2007, vol. 50, # 9, p. 2225 - 2239
[10] Patent: WO2004/2483, 2004, A1, . Location in patent: Page/Page column 23; 41
  • 2
  • [ 71381-75-4 ]
  • [ 91419-53-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 9, p. 2225 - 2239
[2] European Journal of Medicinal Chemistry, 1984, vol. 19, # 2, p. 181 - 186
[3] Patent: US8080566, 2011, B1,
[4] Patent: WO2014/149164, 2014, A1,
[5] Patent: WO2006/123257, 2006, A2,
  • 3
  • [ 498-95-3 ]
  • [ 91419-53-3 ]
Reference: [1] Patent: WO2014/149164, 2014, A1,
  • 4
  • [ 24424-99-5 ]
  • [ 91419-53-3 ]
Reference: [1] Patent: WO2014/149164, 2014, A1,
  • 5
  • [ 91419-53-3 ]
  • [ 162167-97-7 ]
Reference: [1] Patent: WO2004/2483, 2004, A1, . Location in patent: Page/Page column 23; 41
[2] Patent: WO2015/25197, 2015, A1, . Location in patent: Paragraph 000134
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