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[ CAS No. 34803-66-2 ] {[proInfo.proName]}

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Chemical Structure| 34803-66-2
Chemical Structure| 34803-66-2
Structure of 34803-66-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 34803-66-2 ]

CAS No. :34803-66-2 MDL No. :MFCD00006216
Formula : C9H13N3 Boiling Point : -
Linear Structure Formula :- InChI Key :GZRKXKUVVPSREJ-UHFFFAOYSA-N
M.W : 163.22 Pubchem ID :94459
Synonyms :
Pyridylpiperazine

Calculated chemistry of [ 34803-66-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.44
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.6
TPSA : 28.16 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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.73
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : -0.27
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 1.18
Consensus Log Po/w : 0.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.62
Solubility : 3.9 mg/ml ; 0.0239 mol/l
Class : Very soluble
Log S (Ali) : -0.91
Solubility : 20.1 mg/ml ; 0.123 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.502 mg/ml ; 0.00308 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 34803-66-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 34803-66-2 ]

* 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 [ 34803-66-2 ]
  • Downstream synthetic route of [ 34803-66-2 ]

[ 34803-66-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 110-85-0 ]
  • [ 109-04-6 ]
  • [ 34803-66-2 ]
YieldReaction ConditionsOperation in experiment
54% at 150℃; for 0.333333 h; Microwave irradiation Step l0.1 g (0.63 mmol) of 2-bromopyridine and 0.065 g (0.75 mmol) of piperazine was reacted at 150°C for 20 mins in a dried 5 mL microwave reactor provided with nitrogen gas. After cooling to room temperature, the reaction mixture was filtered using a cellite with in concurrence with washing with ethyl acetate, and distilled under a reduced pressure. The resulting residue was subjected to silica gel column chromatography (dichloromethane:methanol=4: l) to obtain l-(pyridin-2-yl)piperazine (yield: 54percent).
36% With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 18 h; Heating / reflux To a 5ml round bottom flask equipped with magnetic stirrer, condenser, and argon inlet, 2-bromopyridine (320mg, 2.0 mmole), piperazine (520mg, 6.0 mmole), Pd2(dba)3 (46mg, 0.050mmole), BINAP (31mg, O.lOmmole), NaO-?- Bu (277mg, 2.8mmole) were added. The reaction mixture was purged with argon for 10 minutes. Toluene (2.0ml) was added. The reaction mixture was heated to reflux for 18hrs. The reaction was partitioned with EtOAc, and filtered through Celite. The solvent was then removed under vacuum. The desired product EPO <DP n="39"/>(74mg, 36percent yield) was isolated via column chromatography with CH2Cl2/MeOH saturated with NH3 (9/1) as eluent. 1H -NMR(400 MHz, CDCl3): δ 3.30-3.09 (m, 4H), 3.51-3.59 (m, 4H), 6.64-6.71 (m, 2H), 7.50-7.55 (m,lH), 8.22-8.27 (m, IH).
Reference: [1] Patent: WO2008/153325, 2008, A1, . Location in patent: Page/Page column 43
[2] Patent: WO2006/47415, 2006, A2, . Location in patent: Page/Page column 37-38
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 2731,2732
[4] Journal of Organic Chemistry, 1953, vol. 18, p. 1484,1487
[5] Patent: WO2008/62276, 2008, A2, . Location in patent: Page/Page column 50
  • 2
  • [ 110-85-0 ]
  • [ 109-09-1 ]
  • [ 34803-66-2 ]
YieldReaction ConditionsOperation in experiment
32% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 20 h; 2-Chloropyridine (0.8 g, 7.2 mmol) was dissolved in N,N-dimethylformamide (10 mL).Then, potassium carbonate (1.0 g, 7.2 mmol) and anhydrous piperazine (1.2 g, 14.4 mmol) were added thereto.Heat to 120 ° C reaction.After 20 hours,Cool to room temperature,Pour the reaction solution into 10 mL of water.Extracted with ethyl acetate (20 mL x 3),The organic phases are combined and the organic phase is dried over anhydrous sodium sulfate.filter,The filtrate is concentrated,Purified by silica gel column chromatography (dichloromethane / methanol (v / v) = 20/1)The title compound was obtained as a yellow oil (0.38 g, 32.0percent).
Reference: [1] Organic Letters, 2016, vol. 18, # 20, p. 5272 - 5275
[2] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2881 - 2884
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2569 - 2581
[4] Patent: CN104163813, 2017, B, . Location in patent: Paragraph 0310; 0327; 0328
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 12, p. 3513 - 3516
[6] Journal of Medicinal Chemistry, 2010, vol. 53, # 21, p. 7549 - 7563
  • 3
  • [ 77278-62-7 ]
  • [ 34803-66-2 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With trifluoroacetic acid In dichloromethane at 30℃; for 1 h;
Stage #2: With sodium hydroxide In dichloromethane; water
A solution of i-butyl 4-(pyridin-2-yl)piperazine-l-carboxylate (500 mg, 1.90 mmol, 1.00 equiv) in DCM/CF3COOH (10/3 mL) was placed in a 50-mL round bottom flask and stirred for 1 h at 30°C in an oil bath. The pH value of the solution was adjusted to 9 with aqueous sodium hydroxide (1M), then extracted with 3x10 mL of dichloromethane. The organic layers combined, dried over anhydrous sodium sulfate, and filtered to remove solids. The resulting solution was concentrated under vacuum, yielding 300 mg (97percent) of l-(pyridin-2-yl)piperazine as yellow oil.
Reference: [1] Patent: WO2011/28947, 2011, A2, . Location in patent: Page/Page column 50; 51
  • 4
  • [ 110-85-0 ]
  • [ 109-09-1 ]
  • [ 34803-66-2 ]
  • [ 64728-49-0 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 34, p. 6913 - 6924
  • 5
  • [ 158399-58-7 ]
  • [ 34803-66-2 ]
Reference: [1] Tetrahedron, 1999, vol. 55, # 44, p. 12829 - 12842
[2] Journal of Organic Chemistry, 1953, vol. 18, p. 1484,1487
  • 6
  • [ 504-29-0 ]
  • [ 821-48-7 ]
  • [ 34803-66-2 ]
Reference: [1] European Journal of Pharmaceutical Sciences, 2016, vol. 88, p. 166 - 177
  • 7
  • [ 109-04-6 ]
  • [ 34803-66-2 ]
Reference: [1] Journal of Organic Chemistry, 1953, vol. 18, p. 1484,1487
[2] Patent: WO2011/28947, 2011, A2,
  • 8
  • [ 34803-66-2 ]
  • [ 3874-54-2 ]
  • [ 1649-18-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3929 - 3936
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 17, p. 5093 - 5109
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