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[ CAS No. 886547-94-0 ] {[proInfo.proName]}

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Chemical Structure| 886547-94-0
Chemical Structure| 886547-94-0
Structure of 886547-94-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 886547-94-0 ]

CAS No. :886547-94-0 MDL No. :MFCD09999194
Formula : C19H21BN2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :KZANVIJXSQABKR-UHFFFAOYSA-N
M.W : 384.26 Pubchem ID :45588137
Synonyms :

Calculated chemistry of [ 886547-94-0 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.32
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 105.28
TPSA : 78.8 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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.48
Log Po/w (WLOGP) : 3.65
Log Po/w (MLOGP) : 2.66
Log Po/w (SILICOS-IT) : 1.2
Consensus Log Po/w : 2.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.63
Solubility : 0.00905 mg/ml ; 0.0000236 mol/l
Class : Moderately soluble
Log S (Ali) : -4.82
Solubility : 0.00585 mg/ml ; 0.0000152 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.06
Solubility : 0.000333 mg/ml ; 0.000000867 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.71

Safety of [ 886547-94-0 ]

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

Application In Synthesis of [ 886547-94-0 ]

* 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 [ 886547-94-0 ]
  • Downstream synthetic route of [ 886547-94-0 ]

[ 886547-94-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 887115-53-9 ]
  • [ 73183-34-3 ]
  • [ 886547-94-0 ]
YieldReaction ConditionsOperation in experiment
100% With potassium acetate In N,N-dimethyl-formamide at 90℃; for 2 h; A solution of 3-iodo-1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridine (4.2 g , 10.9 mmol), bis-pinacolatodiboron (5.6 g, 21.8 mmol), potassium acetate (3.2 g, 32.7 mmol) and Pd(dppf)CI2-complex with dichloromethane (788 mg, 0.982 mmol) inDMF (40 mL) was stirred at 90 0C for 2h in a sealed tube. The solution was cooled by the addition of ice and made basic to pH 12-14 with 6N NaOH. The aqueous phase was extracted with DCM then made acidic to pH ~1 with 6N HCI. The aqeous phase was extracted several times with DCM and the combined fractions were dried (Na2SO4) and concentrated affording the title compound (4.2g, quant.) as a brown solid which was used without further purification; LCMS (m/e) 386 (boronic ester M+H)+, 303 (boronic acid M+H)+.
Reference: [1] Patent: WO2007/76423, 2007, A2, . Location in patent: Page/Page column 53
  • 2
  • [ 880769-95-9 ]
  • [ 73183-34-3 ]
  • [ 886547-94-0 ]
YieldReaction ConditionsOperation in experiment
38% With potassium acetate In tetrahydrofuran for 24 h; Heating / reflux A mixture of compound Id (50.78 g), bis(pinacolato)diboron (42.22 g), [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1 complex with dichloromethane, 12.32 g) and potassium acetate (44.46 g) in THF (3OO mL) was refluxed for 24 hrs. The. reaction was quenched with water and extracted, with ethyl acetate. The combined organic phase was concentrated and the residue was purified on silica gel column (eluted with 100percent dichloromethane and 2percent methanol in dichloromethane) to provide l-benzenesulfonyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (Ie) (22.10 g, 38percent) as a white solid. 1H NMR (400MHz, CDCl3) δ 8.42 (d, J = 4.8 Hz, IH), 8.21 (m, 3H), 8.15 (s, IH), 7.57 (t, J = 7.6 Hz, IH), 7.48 (t, J = 7.6 HZ, 2H), 7.35 (dd, J = 8.0 Hz, 4.8 Hz, IH). MS (ESI) m/z: 385 (M+H)+.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4818 - 4821
[2] Patent: WO2006/50076, 2006, A1, . Location in patent: Page/Page column 62
[3] Patent: US2011/15173, 2011, A1, . Location in patent: Page/Page column 30
[4] Patent: US2011/257187, 2011, A1, . Location in patent: Page/Page column 22
[5] Patent: US2011/257189, 2011, A1, . Location in patent: Page/Page column 35
[6] Patent: WO2008/5457, 2008, A2, . Location in patent: Page/Page column 103
  • 3
  • [ 271-63-6 ]
  • [ 886547-94-0 ]
Reference: [1] Patent: US2011/257187, 2011, A1,
[2] Patent: US2011/257189, 2011, A1,
[3] Patent: WO2008/5457, 2008, A2,
  • 4
  • [ 143141-23-5 ]
  • [ 886547-94-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4818 - 4821
[2] Patent: WO2008/5457, 2008, A2,
  • 5
  • [ 74420-15-8 ]
  • [ 886547-94-0 ]
Reference: [1] Patent: US2011/257187, 2011, A1,
[2] Patent: US2011/257189, 2011, A1,
  • 6
  • [ 98-09-9 ]
  • [ 886547-94-0 ]
Reference: [1] Patent: WO2008/5457, 2008, A2,
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