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[ CAS No. 859850-90-1 ] {[proInfo.proName]}

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Chemical Structure| 859850-90-1
Chemical Structure| 859850-90-1
Structure of 859850-90-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 859850-90-1 ]

CAS No. :859850-90-1 MDL No. :MFCD07772861
Formula : C13H17N3 Boiling Point : -
Linear Structure Formula :- InChI Key :NNYDAONDPGWBRI-UHFFFAOYSA-N
M.W : 215.29 Pubchem ID :7164647
Synonyms :

Calculated chemistry of [ 859850-90-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 71.67
TPSA : 30.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : -4.22
Log Po/w (WLOGP) : 0.39
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 0.35

Druglikeness

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

Water Solubility

Log S (ESOL) : 1.34
Solubility : 4690.0 mg/ml ; 21.8 mol/l
Class : Highly soluble
Log S (Ali) : 4.19
Solubility : 3350000.0 mg/ml ; 15600.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.186 mg/ml ; 0.000863 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 859850-90-1 ]

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 [ 859850-90-1 ]

* 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 [ 859850-90-1 ]
  • Downstream synthetic route of [ 859850-90-1 ]

[ 859850-90-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 109-01-3 ]
  • [ 24964-64-5 ]
  • [ 859850-90-1 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;
Stage #2: With sodium carbonate In dichloromethane; water
Preparation 14: 1-[3-(4-WlethyI-piperazin-1-ylmethyl)-phenyI]-ethanone; STEP A; A mixture of 3-formyl-benzonitrile (1.5 g, 11.45 mmol), N-methyl piperazine (1.49 g, 14.9 mmol) and NaBH(OAc)3 (3.63 g, 17.18 mmol) in DCM (75 ml) and CH3COOH (0.851 ml, 14.9 mmol) was stirred overnight at room temperature, then diluted with DCM and washed with 1 M Na2CO3. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by column chromatography (eluent: DCM/MeOH/NH4OH 97:3:0.5) to give 1.7 g of 3-(4- methyl-piperazin-1-ylmethyl)-benzonitrile. Y= 70percent
70%
Stage #1: With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;
Stage #2: With sodium carbonate In dichloromethane; water
STEP A
A mixture of 3-formyl-benzonitrile (1.5 g, 11.45 mmol), N-methyl piperazine (1.49 g, 14.9 mmol) and NaBH(OAc)3 (3.63 g, 17.18 mmol) in DCM (75 ml) and AcOH (0.851 ml, 14.9 mmol) was stirred at RT overnight and then diluted with DCM and washed with 1 M Na2CO3.
The organic phase was dried over Na2SO4 and evaporated under vacuum.
The crude product was purified by column chromatography (eluent: DCM/MeOH/NH4OH 97:3:0.5) to give 3-(4-methyl-piperazin-1-yl-methyl)-benzonitrile (1.7 g).
Y=70percent
Reference: [1] Patent: WO2007/113249, 2007, A2, . Location in patent: Page/Page column 60-61
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 822 - 839
[3] Patent: EP2033956, 2009, A1, . Location in patent: Page/Page column 13
[4] Patent: WO2006/130075, 2006, A1, . Location in patent: Page/Page column 25-26
  • 2
  • [ 859850-90-1 ]
  • [ 515162-19-3 ]
Reference: [1] Patent: WO2006/130075, 2006, A1, . Location in patent: Page/Page column 25-26
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