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[ CAS No. 162046-50-6 ] {[proInfo.proName]}

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Chemical Structure| 162046-50-6
Chemical Structure| 162046-50-6
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Product Details of [ 162046-50-6 ]

CAS No. :162046-50-6 MDL No. :MFCD04071350
Formula : C12H18N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZTBNOFSSMFDTHM-UHFFFAOYSA-N
M.W : 222.28 Pubchem ID :4409487
Synonyms :

Calculated chemistry of [ 162046-50-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 64.36
TPSA : 64.35 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) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.29
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 1.8
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 1.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.548 mg/ml ; 0.00246 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.117 mg/ml ; 0.000526 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.4
Solubility : 0.0881 mg/ml ; 0.000396 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 162046-50-6 ]

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 [ 162046-50-6 ]

* 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 [ 162046-50-6 ]
  • Downstream synthetic route of [ 162046-50-6 ]

[ 162046-50-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 162046-50-6 ]
  • [ 66655-67-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 656 - 658
  • 2
  • [ 24424-99-5 ]
  • [ 4403-69-4 ]
  • [ 162046-50-6 ]
YieldReaction ConditionsOperation in experiment
96.2% at 20℃; Inert atmosphere; Cooling with ice Take 2-amino-benzylamine (6.0g, 49.2mmol) was dissolved in methylene chloride, N2Protection, under ice-bath stirred and added dropwise (Boc)2O (10.7g, 49.2mmol) in methylene chloride.Bi drops warmed to room temperature and stirred overnight.Thin layer chromatography until the reaction was complete.After completion of the reaction, successively with distilled water, the reaction solution was washed with saturated saline.Dried over anhydrous sodium sulfate, suction filtered, the solvent was distilled off under reduced pressure.Have intermediate 5, 10.5g, a yield of 96.2percent.
79.7% at 20℃; for 4 h; To a solution of 2-(aminomethyl)aniline (10.00 g, 81.85 mmol) in ACN (100 mL) was added Boc20 (17.86 g, 81.85 mmol) in portions. The mixture was stirred at room temperature for 4 h, after which TLC showed the reaction was complete. The mixture was concentrated in vacuo, and the residue was washed with PE/MTBE (50/1), filtered, and filter cake was concentrated in vacuo to afford tert-butyl 2-aminobenzylcarbamate (14.50 g, 79.7percent) as a white solid. 1H NMR: (DMSO; 400MHz) δ 7.27-7.24 (m, 1H), 6.97-6.94 (m, 2H), 6.63 (d, J = 8.00 Hz, 1H), 6.53-6.49 (m, 1H), 5.01 (s, 2H), 3.99 (d, J = 6.00 Hz, 2H), 1.41 (s, 9H). LCMS: (M+H+): 223.
20% With triethylamine In tetrahydrofuran at 20℃; for 16 h; Step a: Preparation of tert-butyl 2-aminobenzylcarbamate (11). To a THF (30 mL) solution of 2-aminobenzyl amine (2.0 g, 16.4 mmol) was added triethylamine (4.60 mL, 32.7 mmol) and di-tert-butyldicarbonate (4.3 g, 19.6 mmol). The reaction mixture was stirred at room temperature for 16 h. The crude reaction mixture was then poured over saturated aqueous NaHCψ3 and the product was then extracted with ethyl acetate. The organic phase was washed with brine and then dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-5percent methanol/dichloromethane) yielding 730 mg (20percent) of 11: 1H NMR (400 MHz, CDCl3) δ 7.12-7.80, (m, IH), 7.00 (d, J = 7.6 Hz, IH), 6.69-6.62 (m, 2H), 4.77, (bs, IH), 4.29-4.11, (m, 4H), 1.43(s, 9H); ESI+ MS: m/z (rel intensity) 223 (80, M+H).
Reference: [1] Patent: CN104016944, 2016, B, . Location in patent: Paragraph 0014-0015; 0046-0047
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 7, p. 1885 - 1889[3] Angew. Chem., 2017, vol. 129, # 7, p. 1911 - 1915,5
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 656 - 658
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1661 - 1669
[6] Patent: US2003/119751, 2003, A1,
[7] Patent: WO2015/154022, 2015, A1, . Location in patent: Paragraph 178-179
[8] Patent: US5767118, 1998, A,
[9] Patent: WO2009/121063, 2009, A2, . Location in patent: Page/Page column 148; 149
[10] Organic Letters, 2002, vol. 4, # 1, p. 63 - 66
[11] Patent: EP1591120, 2005, A1, . Location in patent: Page/Page column 106
[12] Patent: EP2361902, 2011, A1, . Location in patent: Page/Page column 37
[13] Inorganic Chemistry, 2015, vol. 54, # 12, p. 5949 - 5959
  • 3
  • [ 163423-99-2 ]
  • [ 162046-50-6 ]
Reference: [1] Patent: JP2005/314407, 2005, A, . Location in patent: Page/Page column 57
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642
  • 4
  • [ 4403-69-4 ]
  • [ 162046-50-6 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4588 - 4603
  • 5
  • [ 24424-99-5 ]
  • [ 162046-50-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642
[2] Journal of Organic Chemistry, 2017, vol. 82, # 9, p. 4588 - 4603
  • 6
  • [ 24835-08-3 ]
  • [ 162046-50-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642
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