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[ CAS No. 22246-02-2 ] {[proInfo.proName]}

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Chemical Structure| 22246-02-2
Chemical Structure| 22246-02-2
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Product Details of [ 22246-02-2 ]

CAS No. :22246-02-2 MDL No. :MFCD04114866
Formula : C9H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :RQKCSUSXBKSENU-UHFFFAOYSA-N
M.W : 181.62 Pubchem ID :19375637
Synonyms :

Calculated chemistry of [ 22246-02-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.22
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 1.25
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 2.73
Consensus Log Po/w : 1.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.51
Solubility : 0.564 mg/ml ; 0.00311 mol/l
Class : Soluble
Log S (Ali) : -2.09
Solubility : 1.47 mg/ml ; 0.00808 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.0299 mg/ml ; 0.000165 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 22246-02-2 ]

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

Application In Synthesis of [ 22246-02-2 ]

* 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 [ 22246-02-2 ]
  • Downstream synthetic route of [ 22246-02-2 ]

[ 22246-02-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 925-90-6 ]
  • [ 57381-37-0 ]
  • [ 22246-02-2 ]
YieldReaction ConditionsOperation in experiment
34.6%
Stage #1: at 0 - 5℃; for 5 h; Inert atmosphere
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 16 h; Inert atmosphere
To a stirred solution of 2-bromo-5-chlorobenzonitrile (80 g, 370 mmol) in THF (1000 mL) at 0°C was added EtMgBr (370 mL, 1110 mmol) dropwise. The reaction mixture was stilTed at 0-5°C for 5 hours before MeOH (500 mL) was added dropwise. After the solution was stilTed for another 15 mm, NaBH4 (28 g, 740 mmol) was added carefully and the resulting mixture was stirred at room temperature for 16 hours. The reaction solution was then poured into water and exacted with EtOAc (3 x 200 mL). The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crudeproduct, which was purified by column chromatography (petroleum ether: EtOAc =3: 1) to afford the title compound (30 g, 34.6percent) as yellowish oil. MS: 235.5 [M+H’i.
Reference: [1] Patent: WO2014/191340, 2014, A1, . Location in patent: Page/Page column 37; 38
  • 2
  • [ 13078-79-0 ]
  • [ 22246-02-2 ]
Reference: [1] Patent: WO2013/79452, 2013, A1,
[2] Patent: WO2016/55394, 2016, A1,
[3] Patent: WO2014/191340, 2014, A1,
[4] Patent: WO2014/191336, 2014, A1,
[5] Patent: WO2014/191338, 2014, A1,
  • 3
  • [ 13078-79-0 ]
  • [ 22246-02-2 ]
  • [ 1368398-54-2 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9313 - 9328,16
  • 4
  • [ 22246-02-2 ]
  • [ 131002-09-0 ]
YieldReaction ConditionsOperation in experiment
60% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxaneInert atmosphere; Reflux A mixture of 6-chloro-3,4-dihydro-2H-isoquinolin-l-one (181.5 mg, 1 mmol, intermediate A-2) and DDQ (227 mg, 1 mmol) in dioxane (3 mL) was refluxed overnight. After cooling to room temperature, the reaction mixture was treated with satd. aq. NaHC03 solution, and then extracted with ethyl acetate (2 x 10 mL). The organic layers were dried over anhy. Na2S04, filtered, and concentrated in vacuo to afford a crude product which was then purified by silica gel flash chromatography to give title compound (108 mg, 60percent) as a white solid. MS: 180.0 (M+H+).
Reference: [1] Patent: WO2013/79452, 2013, A1, . Location in patent: Page/Page column 133
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