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[ CAS No. 39514-19-7 ] {[proInfo.proName]}

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Chemical Structure| 39514-19-7
Chemical Structure| 39514-19-7
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Product Details of [ 39514-19-7 ]

CAS No. :39514-19-7 MDL No. :MFCD00044512
Formula : C15H19NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :JYFGIESQUYQLGM-UHFFFAOYSA-N
M.W : 261.32 Pubchem ID :419705
Synonyms :

Calculated chemistry of [ 39514-19-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.47
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 76.05
TPSA : 46.61 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) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 1.11
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 2.41
Consensus Log Po/w : 1.84

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.5 mg/ml ; 0.00191 mol/l
Class : Soluble
Log S (Ali) : -2.76
Solubility : 0.453 mg/ml ; 0.00173 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.67
Solubility : 0.056 mg/ml ; 0.000214 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.3

Safety of [ 39514-19-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39514-19-7 ]

* 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 [ 39514-19-7 ]
  • Downstream synthetic route of [ 39514-19-7 ]

[ 39514-19-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 24424-99-5 ]
  • [ 39514-19-7 ]
  • [ 71233-25-5 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With hydrogen In ethanol for 16 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16 h;
STEP A: l -Benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (5.0 g, 16.8 mmol) was stirred in dry ethanol (55 mL). The flask was evacuated and filled with nitrogen prior to the addition of 10percent Pd/C ( 1 .0 g). The resulting suspension was stirred for 16 hours under an atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated to afford a yellow solid (2.9 g). This was immediately dissolved in CH2C12 (100 mL), treated with Boc-anhydride (4.4 g, 20.2 mmol) and DIPEA (4.3 g, 33.6 mmol), and stirred for 16 hours at room temperature. The organics were washed sequentially with HCI (IN), water and brine, dried over magnesium sulfate, filtered, and concentrated to afford 3-oxo-piperidine-l ,4-dicarboxylic acid 1 -te -butyl ester 4-ethyl ester as a clear oil (4.8 g, 100percent yield). MS (ESI) m/e (M+H+): 271.36
94.25% With hydrogen; triethylamine In ethanol for 24 h; A mixture of 1 -benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (1 1 .31 g, 38 mmol), di-t-butyl dicarbonate (8.78 g, 40.2 mmol), Et3N (5.4 ml_, 38.7 mmol) and Pd(OH)2 on carbon (20percent on dry basis-Pearlman's catalyst) (1 .3 g) were taken into EtOH (1 10 ml_). The mixture was hydrogenated at 60 psi for 24 h in a Parr bottle. The catalyst was removed by filtration and the filtrate was concentrated to dryness to tan solid. Crude residue was shaken well with hexane (100 ml_) and filtered. The filtrate was concentrated to yield the title compound (9.70 g, 94.25percent). MS (ESI) mass calcd. for Ci3H2i NO5, 271 .32; 1H NMR (400 MHz, CDCI3) 4.24 (q, J = 7.1 , 2H), 4.03 (s br, 2H), 3.49 (t, J = 5.6, 2H), 2.32 (m, 3H), 1 .47 (s, 9H), 1 .31 (t, J = 7.1 , 3H).
94.25% With hydrogen; triethylamine In ethanol for 24 h; Step A. 3-Oxo-piperidine-1 ,4-dicarboxylic acid 1 -tert-butyl ester 4-ethyl ester. A mixture of 1 -benzyl-3-oxo-piperidine-4-carboxylic acid ethyl ester (1 1 .31 g, 38 mmol), di-t-butyl dicarbonate (8.78 g, 40.2 mmol), Et3N (5.4 ml_, 38.7 mmol) and Pd(OH)2 on carbon (20percent on dry basis-Pearlman's catalyst) (1 .3 g) were taken into EtOH (1 10 ml_). The mixture was hydrogenated at 60 psi for 24 h in a Parr bottle. The catalyst was removed by filtration and the filtrate was concentrated to dryness to tan solid. Crude residue was shaken well with hexane (100 ml_) and filtered. The filtrate was concentrated to yield the title compound (9.70 g, 94.25percent). MS (ESI) mass calcd. for Ci3H2i NO5, 271 .32; 1H NMR (400 MHz, CDCI3) 4.24 (q, J = 7.1 , 2H), 4.03 (s br, 2H), 3.49 (t, J = 5.6, 2H), 2.32 (m, 3H), 1 .47 (s, 9H), 1 .31 (t, J = 7.1 , 3H).
Reference: [1] Patent: WO2011/29842, 2011, A1, . Location in patent: Page/Page column 40
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[3] Patent: WO2015/124941, 2015, A1, . Location in patent: Page/Page column 133; 134
[4] Patent: WO2011/50200, 2011, A1, . Location in patent: Page/Page column 45
[5] Patent: WO2011/50202, 2011, A1, . Location in patent: Page/Page column 44
[6] Patent: US2005/101602, 2005, A1, . Location in patent: Page/Page column 26
[7] Patent: WO2011/103091, 2011, A1, . Location in patent: Page/Page column 88-89
[8] Patent: WO2013/185084, 2013, A1, . Location in patent: Paragraph 0102
  • 2
  • [ 39514-19-7 ]
  • [ 71233-25-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 18, p. 4023 - 4028
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[3] Patent: WO2013/185084, 2013, A1,
  • 3
  • [ 39514-19-7 ]
  • [ 52763-21-0 ]
Reference: [1] Organic Process Research and Development, 2005, vol. 9, # 1, p. 80 - 87
  • 4
  • [ 39514-19-7 ]
  • [ 206111-40-2 ]
Reference: [1] Acta Chemica Scandinavica, 1998, vol. 52, # 4, p. 461 - 468
  • 5
  • [ 67-56-1 ]
  • [ 39514-19-7 ]
  • [ 175406-94-7 ]
Reference: [1] Patent: WO2014/26330, 2014, A1, . Location in patent: Page/Page column 39-40
  • 6
  • [ 39514-19-7 ]
  • [ 3473-63-0 ]
  • [ 62458-96-2 ]
YieldReaction ConditionsOperation in experiment
61.8%
Stage #1: With sodium methylate In methanol at 20℃; for 20 h;
Stage #2: With acetic acid In methanol at 10℃; for 1 h;
To a slurry of sodium methoxide (10.0 g, 185 mmol) in anhydrous MeOH (60 mL) at room temperature was added formamidine acetate (6.60 g, 63.4 mmole) followed by ethyl-l-benzyl-3-oxo-4-piperidine-carboxylate (15.8 g, 52.9 mmol) in one portion. After stirring at rt for 20h, the mixture was cooled to 10°C whereupon 36 mL of water was added followed by 3.8 mL of acetic acid, and the mixture was stirred for an additional hour. The resulting mixture was concentrated and 150 mL of water was added. The solid was collected by filtration and washed with water and air dried. The crude product (9.60 g) was purified by recrystallization from MeOH (~100 mL) to provide 69A as near white needles (7.86 g, 61. 8percent yield). HPLC Ret. Time: 0.46 min. MH+ (m/z) 253. 1H NMR (400 MHz, CDC13, ppm) : 8 2.65 (t, 3H), 2.75 (t, 3H), 3.50 (s, 2H), 3.70 (s, 2H), 7.35 (m, 5H), 7.98 (s, 1H).
2.5 g
Stage #1: With sodium methylate In methanol at 5℃; for 0.5 h;
Stage #2: at 40℃;
The Preparation of Compound 12E:
Sodium methoxide (MeONa, 11 g, 161.65 mmol) was dissolved in methanol (280 mL), cooled to 5° C., and then formamidine acetate (3.0 g, 29.15 mmol) was added. The reaction mixture was stirred for 0.5 hour, and then compound 12D (17 g, 65.1 mmol) was added. The reaction mixture was stirred at 40° C. overnight. The reaction was monitored via TLC (DCM/Methanol=10:1). After the reaction was completed, the reaction mixture was cooled to room temperature, evaporated to remove most of the solvent. The residue was extracted with EA. The organic phase was washed with brine, dried with Na2SO4 and concentrated, to obtain a crude product. The crude product was purified by silica gel chromatography to obtain a purified compound 12E (2.5 g, yield: 16percent) as a light yellow solid.
2.5 g
Stage #1: With sodium methylate In methanol at 5℃; for 0.5 h;
Stage #2: at 40℃;
Sodium methoxide (MeONa, 11 g, 161.65 mmol) was dissolved in methanol (280 mL), cooled to 5° C., and then formamidine acetate (3.0 g, 29.15 mmol) was added. The reaction mixture was stirred for 0.5 hour, and then compound 12D (17 g, 65.1 mmol) was added. The reaction mixture was stirred at 40° C. overnight. The reaction was monitored via TLC (DCM/Methanol=10:1). After the reaction was completed, the reaction mixture was cooled to room temperature, evaporated to remove most of the solvent. The residue was extracted with EA. The organic phase was washed with brine, dried with Na2SO4 and concentrated, to obtain a crude product. The crude product was purified by silica gel chromatography to obtain a purified compound 12E (2.5 g, yield: 16percent) as a light yellow solid.
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9273 - 9285
[2] Patent: WO2005/42537, 2005, A1, . Location in patent: Page/Page column 85
[3] Patent: WO2007/28022, 2007, A2, . Location in patent: Page/Page column 41-42
[4] Patent: US2016/75708, 2016, A1, . Location in patent: Paragraph 0086; 0089
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 3905 - 3912
[6] Patent: KR2015/139962, 2015, A, . Location in patent: Paragraph 0118-0119; 0127-0128
  • 7
  • [ 39514-19-7 ]
  • [ 192869-80-0 ]
Reference: [1] Patent: CN104910158, 2017, B,
  • 8
  • [ 39514-19-7 ]
  • [ 57-13-6 ]
  • [ 62459-02-3 ]
YieldReaction ConditionsOperation in experiment
61% With sodium methylate In methanol at 0 - 60℃; for 96 h; Inert atmosphere To a 0 °C solution of ethyl l-benzyl-3-oxopiperidine-4-carboxylate 1 (12.0 g, 40.4mmol) in MeOH (200 ml) were added urea (5.1g, 84.8 mmol) and NaOMe (12.3 g, 228 mmol) under nitrogen atmosphere, The resulting solution was stirred at 60 °C for 96 hours. The reaction mixture was cooled down to the room temperature and concentrated, the residue was purified by column chromatography (silica gel, dichloromethane/methanol= 10: 1) to provide the desire compound 2 (6.3 g, 61percent). LRMS (M + H+) m/z: calcd 258.29; found 258.30.
Reference: [1] Patent: WO2014/15291, 2014, A1, . Location in patent: Page/Page column 174; 175
  • 9
  • [ 39514-19-7 ]
  • [ 916420-27-4 ]
Reference: [1] Patent: WO2014/15291, 2014, A1,
  • 10
  • [ 39514-19-7 ]
  • [ 1053656-57-7 ]
Reference: [1] Patent: WO2011/29842, 2011, A1,
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9273 - 9285
[5] Patent: US2016/75708, 2016, A1,
[6] Patent: KR2015/139962, 2015, A,
  • 11
  • [ 39514-19-7 ]
  • [ 1142188-60-0 ]
Reference: [1] Patent: WO2011/29842, 2011, A1,
[2] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 2, p. 186 - 190
[4] Patent: US2016/75708, 2016, A1,
[5] Patent: KR2015/139962, 2015, A,
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