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[ CAS No. 52568-28-2 ] {[proInfo.proName]}

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Chemical Structure| 52568-28-2
Chemical Structure| 52568-28-2
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Product Details of [ 52568-28-2 ]

CAS No. :52568-28-2 MDL No. :MFCD08729302
Formula : C8H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :DQSQBZXDMHDHEO-UHFFFAOYSA-N
M.W : 136.19 Pubchem ID :22736922
Synonyms :

Calculated chemistry of [ 52568-28-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.41
TPSA : 38.91 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) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 0.34
Log Po/w (WLOGP) : 1.17
Log Po/w (MLOGP) : 0.55
Log Po/w (SILICOS-IT) : 1.26
Consensus Log Po/w : 1.0

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.28
Solubility : 7.2 mg/ml ; 0.0529 mol/l
Class : Very soluble
Log S (Ali) : -0.72
Solubility : 25.9 mg/ml ; 0.19 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.46
Solubility : 0.474 mg/ml ; 0.00348 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.3

Safety of [ 52568-28-2 ]

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

Application In Synthesis of [ 52568-28-2 ]

* 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 [ 52568-28-2 ]
  • Downstream synthetic route of [ 52568-28-2 ]

[ 52568-28-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 100-70-9 ]
  • [ 917-54-4 ]
  • [ 52568-28-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With cerium(III) chloride In tetrahydrofuran; diethyl ether at -76 - -60℃;
Stage #2: at -76 - 15℃;
Add THF (240 mL) to anhydrous cerium (III) chloride (35 g, 144 mmol) and stir the slurry under nitrogen for 30 minutes. Cool the mixture to -760C in a dry-ice acetone bath. Add a 1.6 M solution of methyl lithium in Et2O (90 mL, 144 mmol) dropwise maintaining the internal reaction temperature below -600C. Stir for 30 minutes after the addition is complete, cool the reaction to -760C, then add 2-cyanopyridine (5 g, 48 mmol) as a solution in THF (20 mL) controlling the addition to keep the reaction below -600C. Stir the mixture in the dry-ice bath for 15 minutes, then remove the bath and allow the reaction to warm to 15 0C. Cool the reaction in the dry-ice bath then add ammonium hydroxide (90 mL) with stirring. Allow the reaction to warm to room temperature with stirring overnight. Decant the solution from the mixture and wash the solids well with THF. Combine the filtrate and washes, then evaporate to give 1 -methyl- l-pyridin-2-yl- ethylamine in quantitative mass balance. 1H NMR (400 MHz, CDCl3): δ 8.52 (d, J= 4.0 Hz, IH), 7.60 (td, J= 7.7, 1.6 Hz, IH), 7.42 (d, J= 7.9 Hz, IH), 7.15-7.08 (m, IH), 1.47 (s, 6H).
73%
Stage #1: With cerium(III) chloride In tetrahydrofuran; diethyl ether at -70℃; for 0.5 h;
Stage #2: at -60 - 23℃; for 2.5 h;
Example 121 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-(at))thiophene-2-sulfonic acid (1 -methyl-1 - pyridin-2-yl) ethylamide hydrochloride Step 1: 1-methyl-1-pyridm-2-yl) ethylamine: Anhydrous cerium chloride (5.10g, 20.69 mmol) is placed in a flask and vacuum dried for 15 min while being heated with a heat gun, then it is cooled to 0°C and tetrahydrofuran (45 mL) is added. After stirring at room temperature for 2 hr, the mixture is cooled to -70°C and treated with 2.0 M methyl lithium in diethyl ether (10.5 mL, 21 mmol). After stirring for an additional period of 0.5 hrs, 2-cyanopyridine (720 mg, 6.91 mmol) in tetrahydrofuran (1 mL) is added. The reaction temperature is kept below-60°C for 0.5 hr, then the temperature is raised to 23°C while stirring for 2 hr. The reaction is quenched with isopropanol (3 mL), filtered through a pad of Celite that is washed thoroughly with dichloromethane. The combined filtrate and wash is concentrated and the residue is purified by flash chromatography on an ISCO Redisep 35 g cartridge eluting with dichloromethane-10percent methanol to afford 1-methyl-1-pyridin-2-yl)ethylamine (688 mg, 73percent yield) as an oil that solidified on standing to yellow solid. 1H NMR (No., ppm) : 1.6 (6H, s), 7.42 (1H), 7.64 (1H), 7.90 (1H), 8.2 (2H, br s), 8.65 (1H).
Reference: [1] Patent: WO2009/131814, 2009, A2, . Location in patent: Page/Page column 43
[2] Journal of the American Chemical Society, 2014, vol. 136, # 33, p. 11574 - 11577
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 51, p. 13588 - 13592[4] Angew. Chem., 2013, vol. 125, # 51, p. 13833 - 13837,5
[5] Patent: WO2005/97750, 2005, A1, . Location in patent: Page/Page column 147-148
[6] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3730 - 3742
[7] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 373 - 377
  • 2
  • [ 100-70-9 ]
  • [ 75-16-1 ]
  • [ 52568-28-2 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: at 0 - 100℃;
Stage #2: With hydrogenchloride; water In toluene at 0℃;
Stage #3: With sodium hydroxide In water
Synthesis of 1-methyl-1-pyridin-2-yl-ethylamine (217), Scheme 8; To a solution of 2-cyanopyridine (33.0 g, 0.32 mol) in 800 mL of toluene was added MeMgBr (566 mL, 2.5 equiv) slowly at 0° C. The mixture was heated at 100° C. overnight, and then quenched with 2 N HCl in an ice bath. The aqueous layer was collected and basified with 4 N NaOH, and then extracted with ether (500 mL.x.3). The combined organic layer was dried and concentrated to give the title compound (35.0 g, 81percent).
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 139 - 149
[2] Patent: US2008/207573, 2008, A1, . Location in patent: Page/Page column 80; 87
[3] Chemical Communications, 2014, vol. 50, # 61, p. 8353 - 8355
[4] Chemistry--A European Journal, 2015, vol. 21, # 1, p. 205 - 209
[5] Chemical Communications, 2015, vol. 51, # 19, p. 4069 - 4072
[6] Chemical Communications, 2016, vol. 52, # 27, p. 4934 - 4937
[7] Organic Letters, 2014, vol. 16, # 15, p. 3904 - 3907
[8] Chemical Communications, 2015, vol. 51, # 24, p. 5093 - 5096
[9] Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8219 - 8226
[10] Organic Letters, 2014, vol. 16, # 21, p. 5644 - 5647
[11] Advanced Synthesis and Catalysis, 2017, vol. 359, # 23, p. 4117 - 4121
[12] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2241 - 2246
  • 3
  • [ 100-70-9 ]
  • [ 52568-28-2 ]
Reference: [1] Patent: WO2008/4698, 2008, A2, . Location in patent: Page/Page column 129-130
  • 4
  • [ 1192356-19-6 ]
  • [ 52568-28-2 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 373 - 377
  • 5
  • [ 100-70-9 ]
  • [ 917-64-6 ]
  • [ 52568-28-2 ]
Reference: [1] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 23, p. 3728 - 3743
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