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[ CAS No. 129722-25-4 ] {[proInfo.proName]}

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Chemical Structure| 129722-25-4
Chemical Structure| 129722-25-4
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Product Details of [ 129722-25-4 ]

CAS No. :129722-25-4 MDL No. :MFCD00892073
Formula : C23H25Cl2N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CDONPRYEWWPREK-UHFFFAOYSA-N
M.W : 446.37 Pubchem ID :10114519
Synonyms :
OPC-14857;DM-14857
Chemical Name :7-(4-(4-(2,3-Dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2(1H)-one

Calculated chemistry of [ 129722-25-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.35
Num. rotatable bonds : 7
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 131.28
TPSA : 48.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.1
Log Po/w (XLOGP3) : 4.91
Log Po/w (WLOGP) : 4.05
Log Po/w (MLOGP) : 3.86
Log Po/w (SILICOS-IT) : 5.45
Consensus Log Po/w : 4.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.63
Solubility : 0.00104 mg/ml ; 0.00000233 mol/l
Class : Moderately soluble
Log S (Ali) : -5.67
Solubility : 0.000963 mg/ml ; 0.00000216 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.38
Solubility : 0.00000187 mg/ml ; 0.0000000042 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.98

Safety of [ 129722-25-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 129722-25-4 ]

* 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 [ 129722-25-4 ]
  • Downstream synthetic route of [ 129722-25-4 ]

[ 129722-25-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 129722-12-9 ]
  • [ 129722-25-4 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 0.666667 h; Inert atmosphere; large scale reaction
Stage #2: With sodium hydroxide In tetrahydrofuran; water
Example 1
Large scale synthesis of dehydroaripiprazole [7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)quinolin-2(1H)-one] (Compound 1; Formula VI)
Aripiprazole (Formula VIA; 15 g, 0.03 mol) was dissolved in anhydrous tetrahydrofuran (360 mL).
Trifluoroacetic acid (12 mL, 0.16 mol) was added to the clear solution. 1,2-Dichloro-4,5-dicyano quinone (24.3 g, 0.11 mol) was added and the mixture was stirred at room temperature under nitrogen atmosphere.
The reaction was stirred for 40 minutes and TLC showed no starting material remaining Water (1.5 L) was added then reaction mixture basified with 50percent aq NaOH until pH 12.
The reaction mixture was extracted with dichloromethane (3*μL) and the combined organics were dried (MgSO4) to give the crude product.
This was purified by column chromatography on silica eluting with dichloromethane to 10percent methanol/dichloromethane.
The product was further purified by recrystallisation from 2-propanol to give the desired product (13.7 g, 92percent) as an off white solid. 1H-NMR (400 MHz, CDCl3) δ 12.33 (1H, br s), 7.72 (1H, d), 7.42 (1H, d), 7.16-7.11 (2H, m), 6.98-6.93 (1H, dd), 6.83-6.79 (2H, m), 6.53 (1H, d), 4.10 (2H, t), 3.09 (4H, br s), 2.67 (4H, br s), 2.52 (2H, t), 1.93-1.70 (4H, m). LCMS (acidic method) [M+H]+ 446.02, rt 14.246 min.
Reference: [1] Patent: US2011/275803, 2011, A1, . Location in patent: Page/Page column 60-61
[2] Crystal Growth and Design, 2013, vol. 13, # 5, p. 2036 - 2046
[3] Heterocyclic Communications, 2005, vol. 11, # 6, p. 485 - 490
  • 2
  • [ 41202-77-1 ]
  • [ 203395-59-9 ]
  • [ 129722-25-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 658 - 667
  • 3
  • [ 70500-72-0 ]
  • [ 129722-25-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 658 - 667
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7141 - 7153
  • 4
  • [ 203395-59-9 ]
  • [ 129722-25-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7141 - 7153
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