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[ CAS No. 1086062-66-9 ] {[proInfo.proName]}

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Chemical Structure| 1086062-66-9
Chemical Structure| 1086062-66-9
Structure of 1086062-66-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1086062-66-9 ]

CAS No. :1086062-66-9 MDL No. :MFCD16038929
Formula : C25H17F2N5O3S Boiling Point : No data available
Linear Structure Formula :- InChI Key :CGBJSGAELGCMKE-UHFFFAOYSA-N
M.W :505.50 Pubchem ID :25167777
Synonyms :
Omipalisib

Calculated chemistry of [ 1086062-66-9 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 28
Fraction Csp3 : 0.04
Num. rotatable bonds : 6
Num. H-bond acceptors : 9.0
Num. H-bond donors : 1.0
Molar Refractivity : 129.52
TPSA : 115.34 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.08
Log Po/w (XLOGP3) : 3.32
Log Po/w (WLOGP) : 6.57
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 4.28
Consensus Log Po/w : 3.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.25
Solubility : 0.00287 mg/ml ; 0.00000569 mol/l
Class : Moderately soluble
Log S (Ali) : -5.42
Solubility : 0.00193 mg/ml ; 0.00000382 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -10.61
Solubility : 0.0000000123 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.57

Safety of [ 1086062-66-9 ]

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

Application In Synthesis of [ 1086062-66-9 ]

* 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 [ 1086062-66-9 ]
  • Downstream synthetic route of [ 1086062-66-9 ]

[ 1086062-66-9 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 1086063-46-8 ]
  • [ 1086063-18-4 ]
  • [ 1086062-66-9 ]
YieldReaction ConditionsOperation in experiment
76% With potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 100℃; for 3 h; b)
2,4-difluoro-N-{2-(methyloxy)-5-[4-(4-pyridazinyl)-6-quinolinyl]-3-pyridinyl}benzenesulfonamide
A slurry of 6-bromo-4-(4-pyridazinyl)quinoline (4.8 g, 16.78 mmol), bis(pinacolato)diboron (4.69 g, 18.45 mmol), PdCl2(dppf)-CH2Cl2 (530 mg, 0.649 mmol) and potassium acetate (3.29 g, 33.6 mmol) in anhydrous 1,4-dioxane (120 ml) was heated at 100° C. for 3 h.
The complete disappearance of the starting bromide was observed by LCMS.
The reaction was then treated with N[5-bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (6.68 g, 17.61 mmol) and another portion of PdCl2(dppf)-CH2Cl2 (550 mg, 0.673 mmol), then heated at 110° C. for 16 h.
The reaction was allowed to cool to room temperature, filtered, and concentrated.
Purification of the residue by chromatography (Analogix; 5percent MeOH/5percent CH2Cl2/90percent EtOAC) gave 6.5 g (76percent) desired product. MS(ES)+ m/e 505.9 [M+H]+.
Reference: [1] Patent: US2013/317037, 2013, A1, . Location in patent: Paragraph 0104
  • 2
  • [ 1086063-46-8 ]
  • [ 1086062-66-9 ]
YieldReaction ConditionsOperation in experiment
717 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxaneReflux A suspension of 7 (570.0 mg, 2.0 mmol), bis(pinacolato)diboron (559.4 mg, 2.2 mmol), PdCl2(dppf)-CH2Cl2 (82.0 mg, 0.1 mmol) and KOAc (392.7 mg, 4.0 mmol) in anhydrous 1,4-dioxane (20 mL) was stirred and heated at reflux for 3 h. The reaction mixture was treated with 19 (790.0 mg, 2.1 mmol), 2 M Na2CO3 (4 mL), and another portion of PdCl2(dppf)-CH2Cl2 (82.0 mg, 0.2 mmol), then heated at reflux overnight. After the reaction mixture was allowed to cool to rt, it was filtered through a pad of Celite, washed with abundant CH2Cl2, and concentrated in vacuo. The crude product was purified by silica gel column (90:5:5 EtOAc/CH2Cl2/MeOH) to afford 22 (717.0 mg, 71percent) as a pale brown solid, mp 183-184 °C (lit1 187-189 °C). 1H NMR (DMSO-d6) δ 10.3 (br s, 1H, NH), 9.57-9.56 (m, 1H, Ar-H), 9.47 (dd, J = 5.0, 1.0 Hz, 1H, Ar-H), 9.05 (d, J = 4.5 Hz, 1H, Ar-H), 8.42 (d, J = 4.5 Hz, 1H, Ar-H), 8.25 (d, J = 8.5 Hz, 1H, Ar-H), 8.12 (dd, J = 9.0, 2.0 Hz, 1H, Ar-H), 8.07 (dd, J = 5.0, 2.0 Hz, 1H, Ar-H), 7.94 (dd, J = 4.0, 2.0 Hz, 2H, Ar-H), 7.74-7.70 (m, 1H, Ar-H), 7.67 (d, J = 4.5 Hz, 1H, Ar-H), 7.58-7.53 (m, 1H, Ar-H), 7.19 (td, J = 8.5, 2.5 Hz, 1H, Ar-H), 3.64 (s, 3H, OCH3). HRMS (ESI, m/z): calcd for C25H18N5O3F2S ([M+H]+) 506.1098, found 506.1101.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 3
  • [ 884495-39-0 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
[2] Patent: US2013/317037, 2013, A1,
  • 4
  • [ 67443-38-3 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
[2] Patent: US2013/317037, 2013, A1,
  • 5
  • [ 152684-30-5 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
[2] Patent: US2013/317037, 2013, A1,
  • 6
  • [ 15862-34-7 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 7
  • [ 65340-70-7 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 8
  • [ 927801-23-8 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 9
  • [ 1086062-75-0 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 10
  • [ 1086063-18-4 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 11
  • [ 145369-94-4 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
  • 12
  • [ 187278-01-9 ]
  • [ 1086062-66-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 4, p. 1569 - 1574
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