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[ CAS No. 163765-44-4 ] {[proInfo.proName]}

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Chemical Structure| 163765-44-4
Chemical Structure| 163765-44-4
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Product Details of [ 163765-44-4 ]

CAS No. :163765-44-4 MDL No. :MFCD02683205
Formula : C10H20N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FMLPQHJYUZTHQS-MRVPVSSYSA-N
M.W : 200.28 Pubchem ID :2756811
Synonyms :
Chemical Name :(R)-1-Boc-3-Methylpiperazine

Calculated chemistry of [ 163765-44-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.31
TPSA : 41.57 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) : 2.73
Log Po/w (XLOGP3) : 0.89
Log Po/w (WLOGP) : 0.45
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.6
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 7.2 mg/ml ; 0.0359 mol/l
Class : Very soluble
Log S (Ali) : -1.35
Solubility : 8.99 mg/ml ; 0.0449 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.44
Solubility : 7.29 mg/ml ; 0.0364 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.72

Safety of [ 163765-44-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 163765-44-4 ]

* 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 [ 163765-44-4 ]
  • Downstream synthetic route of [ 163765-44-4 ]

[ 163765-44-4 ] Synthesis Path-Upstream   1~4

  • 1
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  • [ 75336-86-6 ]
  • [ 163765-44-4 ]
YieldReaction ConditionsOperation in experiment
84% at 0 - 20℃; for 4 h; To a solution of (R)-methylpiperazine (400 mg) in dichloromethane (20 mL) at 0 0C was added di-tert-butyl dicarbonate (871 mg). The reaction was stirred at room <n="194"/>temperature for 4 h and then quenched with water (20 mL) and extracted into dichloromethane (2 x 40 mL). The combined organics were washed with saturated aqueous brine solution (40 mL), dried (MgSO4) and concentrated to give (R)-3-methyl-piperazine-l- carboxylic acid tert-butyl ester as a white solid (669 mg, 84percent).
50% at 0 - 20℃; (R)-2-methylpiperazine (5.025 g, 50.2 mmol) was dissolved in DCM (100 mL). A solution of boc anhydride (5.47 g, 25.1 mmol) in DCM (50 mL) was added dropwise at 0° C. The reaction mixture was stirred at rt for 1 h. The solution was filtered and concentrated under reduced pressure. Water (100 mL) was added to the residue, which was filtered again. The filtrate was saturated with K2CO3 and extracted with Et2O (3.x.150 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide 5.04 g title compound (50percent) as a solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.03 (d, J=6.3 Hz, 3H) 1.45 (s, 9H) 1.56 (s, 1H) 2.30-2.46 (m, 1H) 2.65-2.72 (m, 1H) 2.74-2.76 (m, 2H) 2.93-2.95 (m, 1H) 3.93 (br s, 2H).
50% at 0 - 20℃; (R)-2-methylpiperazine (5.025 g, 50.2 mmol) was dissolved in DCM (100 mL).
A solution of boc anhydride (5.47 g, 25.1 mmol) in DCM (50 mL) was added dropwise at 0° C.
The reaction mixture was stirred at rt for 1 h.
The solution was filtered and concentrated under reduced pressure. H2O (100 mL) was added to the residue, which was filtered again.
The filtrate was saturated with K2CO3 and extracted with Et2O (3*150 mL).
The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide 5.04 g Intermediate D (50percent) as a solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.03 (d, J=6.3 Hz, 3H) 1.45 (s, 9H) 1.56 (s, 1H) 2.30-2.46 (m, 1H) 2.65-2.72 (m, 1H) 2.74-2.76 (m, 2H) 2.93-2.95 (m, 1H) 3.93 (br s, 2H).
Intermediate D is also commercially available from Lanzhou Boc Chemical Co.
Reference: [1] Patent: WO2008/70740, 2008, A1, . Location in patent: Page/Page column 191
[2] Patent: US2010/216812, 2010, A1, . Location in patent: Page/Page column 45
[3] Patent: US2011/201622, 2011, A1, . Location in patent: Page/Page column 14
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 11, p. 3282 - 3285
[5] Patent: US2005/70549, 2005, A1,
[6] Patent: WO2006/24823, 2006, A1, . Location in patent: Page/Page column 159
[7] Patent: WO2007/70683, 2007, A2, . Location in patent: Page/Page column 108
[8] Patent: US2016/31908, 2016, A1, . Location in patent: Paragraph 1671; 1672
[9] Patent: EP1726590, 2006, A1, . Location in patent: Page/Page column 80
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  • [ 75336-86-6 ]
  • [ 163765-44-4 ]
Reference: [1] Patent: US2003/153556, 2003, A1,
  • 3
  • [ 58632-95-4 ]
  • [ 75336-86-6 ]
  • [ 163765-44-4 ]
Reference: [1] Patent: WO2008/134035, 2008, A1, . Location in patent: Page/Page column 123; 142
  • 4
  • [ 120737-59-9 ]
  • [ 1394957-82-4 ]
  • [ 163765-44-4 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 71, p. 8892 - 8894
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