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[ CAS No. 223796-20-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 223796-20-1
Chemical Structure| 223796-20-1
Chemical Structure| 223796-20-1
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Product Details of [ 223796-20-1 ]

CAS No. :223796-20-1 MDL No. :MFCD06409205
Formula : C10H15N3 Boiling Point : -
Linear Structure Formula :- InChI Key :JBOVXXZNZSULJJ-UHFFFAOYSA-N
M.W : 177.25 Pubchem ID :10654891
Synonyms :

Calculated chemistry of [ 223796-20-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.4
TPSA : 28.16 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 0.68
Log Po/w (WLOGP) : 0.12
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 1.39
Consensus Log Po/w : 0.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.64
Solubility : 4.03 mg/ml ; 0.0228 mol/l
Class : Very soluble
Log S (Ali) : -0.85
Solubility : 25.1 mg/ml ; 0.142 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.8
Solubility : 0.282 mg/ml ; 0.00159 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.02

Safety of [ 223796-20-1 ]

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

Application In Synthesis of [ 223796-20-1 ]

* 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 [ 223796-20-1 ]
  • Downstream synthetic route of [ 223796-20-1 ]

[ 223796-20-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 223797-48-6 ]
  • [ 223796-20-1 ]
YieldReaction ConditionsOperation in experiment
85% With trifluoroacetic acid In dichloromethane for 15 h; A solution of 1-(3-pyridyl)-4-tert-butoxycarbonylhomopiperazine (0.91 g, 3.3 mmol), trifluoroacetic acid (7.5 g, 66 mmol) and dichloromethane (30 ml) was stirred for 15 h.
The mixture was evaporated.
Sodium hydroxide (30 ml, 4 M) was added.
The product was extracted two times with dichloromethane (30 ml) and isolated as an oil.
Yield 0.50 g, 85percent.
The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid.
Mp 172.1-172.9° C.
84% With trifluoroacetic acid In dichloromethane at 20℃; for 16 h; General procedure: 58 was deprotected as described for 28 from a mixture of 58 (948 mg, 3.42 mmol) and TFA (5.23 mL, 68.4 mmol) yielding 1-(pyridin-3-yl)-1,4-diazepane as a yellow oil (507 mg, 84percent). 1H NMR(CDCl3, 400 MHz) d 8.13 (d, 1H, J 3.1 Hz), 7.92 (dd, 1H, J 4.5,1.3 Hz), 7.10 (dd, 1H, J 8.5, 4.6 Hz), 6.95 (ddd, 1H, J 8.6, 3.1,1.3 Hz), 3.62e3.54 (m, 4H), 3.05 (t, 2H, J 5.3 Hz), 2.85 (t, 2H,J 5.8 Hz), 2.07 (s, 1H), 1.93 (p, 2H, J 6.0 Hz). 13C NMR (CDCl3,101 MHz) d 144.40, 137.49, 134.54, 123.84, 117.91, 51.45, 48.19, 47.93,47.89, 29.24. Compound 30 was prepared as described for 28 from amixture of 1-(pyridin-3-yl)-1,4-diazepane (100 mg, 0.56 mmol),benzaldehyde (57 mL, 0.56 mmol), and NaBH(OAc)3 (178 mg,0.84 mmol) affording the product as a yellow oil (104 mg, 69percent). 1HNMR (CDCl3, 400 MHz) d 8.12 (d, 1H, J 3.0 Hz), 7.93 (dd, 1H, J 4.6,1.3 Hz), 7.34e7.28 (m, 4H), 7.28e7.23 (m, 2H), 7.10 (ddd, 1H, J 8.5,4.6, 0.6 Hz), 6.94 (ddd, 1H, J 8.6, 3.1, 1.3 Hz), 3.65 (s, 2H), 3.54 (dt,4H, J 13.3, 5.6 Hz), 2.78 (t, 2H, J 5.0 Hz), 2.65 (t, 2H, J 5.6 Hz),1.98 (p, 2H, J 5.9 Hz). 13C NMR (CDCl3, 101 MHz) d 145.07, 138.94,137.23, 134.47, 128.97 (2C), 128.44 (2C), 127.27, 123.72,117.93, 62.48,55.07, 54.75, 48.74, 47.99, 27.62. 1-Benzyl-4-(pyridin-3-yl)-1,4-diazepane oxalate. The free amine of 30 (104 mg, 0.39 mmol)was converted into the oxalate salt as described under the generalprocedure affording an orange solid (113 mg, 81percent). Mp:124.0e124.8 C. 1H NMR (D2O, 400 MHz) d 8.16 (d, 1H, J 3.0 Hz),8.06 (d, 1H, J 5.3 Hz), 7.89 (ddd, 1H, J 9.1, 3.0, 1.1 Hz), 7.82 (dd,1H, J 9.0, 5.3 Hz), 7.60e7.53 (m, 5H), 4.44 (s, 2H), 3.92 (t, 2H,J 4.6 Hz), 3.78 (s, 4H), 3.62 (t, 2H, J 6.1 Hz), 3.59e3.44 (m, 3H),2.40e2.34 (m, 2H). 13C NMR (D2O, 101 MHz) d 170.15 (2C), 147.06,131.23 (2C), 130.32, 129.34 (2C), 128.79, 128.58, 127.42, 127.07,124.30, 61.07, 53.93, 53.71, 46.61, 42.97, 23.45.; 3.2.24. 1-(6-Bromopyridin-3-yl)-4-(3-phenylpropyl)-1,4-diazepane(28); A solution of 58 (598 mg, 1.68 mmol) and TFA (2.58 mL, 33.7 mmol) in DCM (20 mL) was stirred at rt for 16 h.
The reaction mixture was evaporated in vacuo.
The residue was added aq NaOH solution (4 M, 20 mL) and extracted with DCM (3 * 100 mL).
The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo giving 1-(6-bromopyridin-3-yl)-1,4-diazepane as a yellow oil (274 mg, 64percent) that crystallizes over time.
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2217 - 2226
[2] Patent: US2004/72823, 2004, A1, . Location in patent: Page/Page column 16
[3] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 425 - 444
  • 2
  • [ 626-55-1 ]
  • [ 223796-20-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2217 - 2226
  • 3
  • [ 112275-50-0 ]
  • [ 223796-20-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 11, p. 2217 - 2226
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