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[ CAS No. 150008-24-5 ] {[proInfo.proName]}

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Chemical Structure| 150008-24-5
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Product Details of [ 150008-24-5 ]

CAS No. :150008-24-5 MDL No. :MFCD09953970
Formula : C10H18N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :LDLQTMSUZKHEHY-UHFFFAOYSA-N
M.W : 214.26 Pubchem ID :15462924
Synonyms :

Calculated chemistry of [ 150008-24-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.01
TPSA : 62.13 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) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 0.82
Log Po/w (WLOGP) : 1.47
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.86
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.49
Solubility : 6.98 mg/ml ; 0.0326 mol/l
Class : Very soluble
Log S (Ali) : -1.71
Solubility : 4.21 mg/ml ; 0.0196 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.97
Solubility : 23.0 mg/ml ; 0.107 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.42

Safety of [ 150008-24-5 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P280-P210-P240-P264-P270-P301+P310-P330-P370+P378-P403+P233-P405-P501 UN#:1325
Hazard Statements:H228-H302-H317-H319-H341-H351 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 150008-24-5 ]

* 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 [ 150008-24-5 ]
  • Downstream synthetic route of [ 150008-24-5 ]

[ 150008-24-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 150008-24-5 ]
  • [ 190900-21-1 ]
YieldReaction ConditionsOperation in experiment
84% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 70℃; Inert atmosphere To a solution of ketoxime (0.01 mol) in THF (10 mL) was added T3P (15 mol percent, 50percent soln in EtOAc) and the resulting reaction mixture was stirred at reflux for 1-4 h under nitrogen atmosphere. When the reaction was completed as confirmed by TLC, the solvent was removed under vacuum and the residue was diluted with water (20 mL). The product was extracted with ethyl acetate (2 .x. 20 mL) and the combined organic phase was washed with saturated NaHCO3 solution (1 .x. 10 mL) and brine. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford the desired amides in good purity.
48%
Stage #1: With sodium carbonate In water; acetone for 0.0833333 h;
Stage #2: With p-toluenesulfonyl chloride In water; acetone at 20℃;
To a solution of intermediate I-49 (11 g, 50 mmol, 1.0 eq) in acetone (60 mL) was added a solution of Na2CO3 (16 g, 150 mmol, 3.0 eq) in water (80 mL) and the reaction mixture was stirred for 5 minutes. A solution of p-toluenesulfonyl chloride (14 g, 75 mmol, 1.5 eq) in acetone (20 mL) was added slowly and the reaction mixture was stirred at room temperature for 3 hours. Excess solvent was removed by evaporation, water was added and the reaction mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous MgSO4, the solids were removed by filtration and the filtrate was concentrated by evaporation. The crude reaction product was purified by silica gel column chromatography to give intermediate I-50 (5.0 g, 48percent). MS (ESI): m/z 159.1 (M+H+).
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
[2] Patent: US2010/204214, 2010, A1, . Location in patent: Page/Page column 108
[3] Patent: WO2006/56877, 2006, A2, . Location in patent: Page/Page column 24
[4] Tetrahedron Letters, 2009, vol. 50, # 2, p. 148 - 151
  • 2
  • [ 150008-24-5 ]
  • [ 190900-21-1 ]
Reference: [1] Patent: EP1477490, 2004, A1, . Location in patent: Page 109
  • 3
  • [ 79099-07-3 ]
  • [ 150008-24-5 ]
YieldReaction ConditionsOperation in experiment
100% With hydroxylamine hydrochloride; sodium acetate In methanol; waterReflux All of the oxime substrates used in this investigation were synthesized in quantitative yields by refluxing a mixture of 1 equiv of the corresponding ketones or aldehydes, 1.6 equiv of hydroxylamine hydrochloride, and 2.0 equiv of sodium acetate in aqueous methanol.
100% With hydroxylamine hydrochloride; sodium acetate In ethanol; water To a solution of tert-butyl 4-piperidinone carboxylate in ethanol (400 mL), hydroxylamine hydrochloride (29.34 g) and sodium acetate (34.64 g) were added, and stirred at 100°C for seven hours.
The reaction mixture was cooled to room temperature, and the filtrate obtained by filtering off the solid was concentrated under reduced pressure.
Water was added to the residue, and extracted twice with ethyl acetate.
The combined organic layer was washed in a saturated aqueous solution of sodium bicarbonate and saturated saline, and then dried on anhydrous magnesium sulfate, and filtered.
The solvent was evaporated under reduced pressure, dried under vacuum to obtain a title compound (quantitative yield) as a white solid compound.
1H-NMR (400 MHz, DMSO-d6) δ(ppm): 1.46 (s, 9H), 2.27 (m, 2H), 2.49 (m, 2H), 3.36-3.52 (m, 4H), 10.50 (s, 1H).
96%
Stage #1: With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 1 h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
Hydroxylamine hydrochloride (2.50 g, 36.0 mmol) was added to a solution of l-Boc-4-piperidone (6.10 g, 30.0 mmol) and sodium acetate (2.95 g, 36.0 mmol) in ethanol (60 ml) and the whole was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (120 ml) and washed with saturated aqueous NaHCO3 (30 ml) and brine, dried over MgSO4 and concentrated in vacuo. The residual solid was recrystallized from ethyl acetate/n-hexane to give tert-butyl 4- (hydroxyimino)piperidine-1-carboxylate (6.18 g, 96 percent) as a white solid.
65% With hydroxylamine hydrochloride In pyridine at 65℃; for 1 h; To a solution of N-t-butoxycarbonyl-4-piperidone 1 (15 g, 75.3 mmol) in pyridine (50 mL) was added hydroxylamine .bul. HCl (5.23 g, 75.3 mmol). The mixture was heated in an oil bath at 65 °C for 1 h. After cooling, pyridine was removed under reduced pressure and the residue was dried under high vacuum overnight to give a solid. To this solid was added water (100 mL) and the mixture was sonicated. The precipitate was filtered and washed with water then dried under high vacuum to give the oxime derivative of compound 1 (10.5 g, 65percent); FAB MS [M+1]+ 215.3. The oxime (10 g, 46.67 mmol) was dissolved in absolute EtOH (100 mL) followed by the addition of Raney Ni (29 g, washed with absolute EtOH). The mixture was hydrogenated in a Parr shaker at 50 psi overnight. After reaction was complete, the Raney Ni was filtered off (caution; risk of fire) and the filtrate was concentrated to give compound 2 (9.2 g, 46 mmol,98percent yield) as an oil which solidified under high vacuum drying. FAB MS [M+1]+ 201.3. To a solution of the bromoacetamide derivative 3 (3.0g,6.2 mmol) (prepared in Example 3) in CH2Cl2 (62 mL) at -10 °C were added Huenig's base (1.2 mL, 6.82 mmol) and compound 2 (2.48 g, 12.39 mmol). The solution was gradually warmed to RT overnight. After reaction was complete, CH2Cl2 (300 mL) was added and the mixture was washed with brine (100 mL, 3x), dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give a light yellow solid which was purified by flash chromatography on silica gel (200 g), eluting with 5percent [NH4OH/MeOH (1:9)] /CH2Cl2 to give a 71percent yield of the title compound 4 as a white solid (2.66 g, 4.4 mmol), m.p. 78-81 °C; FAB MS [M+1]+35Cl 603.1; Calcd. for C31H40N4O4Cl2, C, 61.69; H, 6.68; N,9.28; Cl,11.74. Found: C, 61.33; H, 6.94; N, 9.17; Cl, 11.27.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2942 - 2945
[2] Tetrahedron Letters, 2010, vol. 51, # 24, p. 3216 - 3217
[3] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
[4] Patent: EP1477490, 2004, A1, . Location in patent: Page 109
[5] Patent: WO2008/150447, 2008, A1, . Location in patent: Page/Page column 206
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 983 - 988
[7] Patent: EP937069, 2006, B1, . Location in patent: Page/Page column 46-47
[8] Patent: WO2006/56877, 2006, A2, . Location in patent: Page/Page column 23-24
[9] Tetrahedron Letters, 2009, vol. 50, # 2, p. 148 - 151
[10] Patent: US2010/204214, 2010, A1, . Location in patent: Page/Page column 108
[11] Patent: WO2017/156177, 2017, A1, . Location in patent: Paragraph 00318
[12] Patent: WO2006/105056, 2006, A2, . Location in patent: Page/Page column 16-17
  • 4
  • [ 79099-07-3 ]
  • [ 497-19-8 ]
  • [ 150008-24-5 ]
YieldReaction ConditionsOperation in experiment
87% With hydroxylamine hydrochloride In methanol a
N-tert-Butoxycarbonyl-4-piperidone oxime
To a stirred suspension of hydroxylamine hydrochloride (0.84 g, 12.0 mmol) in methanol (10 mL) at 0° C. was added solid Na2 CO3 (0.64 g, 6.0 mmol).
The mixture was stirred for ca. 5 min. N-t-Boc-4-piperidone (1.99 g, 10.0 mmol) was added and the mixture was stirred for ca 2 h.
The reaction mixture was concentrated in vacuo to ca.
half its original volume, then diluted with saturated NaHCO3 (100 mL) and extracted with CHCl3 (4*50 mL).
The combined organic layers were dried over Na2 SO4, filtered, and concentrated in vacuo to yield 1.86 g (87percent) of the desired product as a tan solid. MS (ES+) m/z 215.0 [M+H]+.
Reference: [1] Patent: US6077857, 2000, A,
  • 5
  • [ 79099-07-3 ]
  • [ 150008-24-5 ]
Reference: [1] Patent: US5276041, 1994, A,
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