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[ CAS No. 1002309-52-5 ] {[proInfo.proName]}

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Chemical Structure| 1002309-52-5
Chemical Structure| 1002309-52-5
Structure of 1002309-52-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1002309-52-5 ]

CAS No. :1002309-52-5 MDL No. :MFCD11044683
Formula : C12H18BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :IJUNZKOKAXJGRQ-UHFFFAOYSA-N
M.W : 235.09 Pubchem ID :45480194
Synonyms :

Calculated chemistry of [ 1002309-52-5 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.58
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 68.44
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.93
Log Po/w (WLOGP) : 0.68
Log Po/w (MLOGP) : 0.73
Log Po/w (SILICOS-IT) : 0.88
Consensus Log Po/w : 0.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.08
Solubility : 1.96 mg/ml ; 0.00834 mol/l
Class : Soluble
Log S (Ali) : -1.37
Solubility : 10.1 mg/ml ; 0.0431 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.187 mg/ml ; 0.000794 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.97

Safety of [ 1002309-52-5 ]

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 [ 1002309-52-5 ]

* 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 [ 1002309-52-5 ]
  • Downstream synthetic route of [ 1002309-52-5 ]

[ 1002309-52-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 81971-39-3 ]
  • [ 73183-34-3 ]
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YieldReaction ConditionsOperation in experiment
23.6% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2 h; Microwave irradiation A solution of 5-bromo-1-methylpyridin-2-one (200.0 mg, 1.06 mmol), bis(pinacolato)diboron (410.0 mg, 1.61 mmol), potassium acetate (270 mg, 2.67 mmol), Pd (dppf)Cl2 (80 mg, 0.11 mmol) in dioxane (5 mL) was heated at 100° C. for 2 h under microwave.
The mixture was filtered, washed with water and extracted with ethyl acetate (20 mL*3).
The combined organics were dried over Na2SO4, filtered and concentrated to give the crude title compound (59.0 mg, 23.6percent). LCMS (M+H)+ 236.
160 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In ethylene glycol at 80℃; for 3 h; To a stirred suspension of 5-bromo-l-methylpyridin-2(lH)-one (470 mg, 2.49 mmol), potassium acetate (736 mg, 7.49 mmol) and bis(pinacolato)diboron (952 mg, 3.74 mmol) in degassed polyethylene glycol-400 (15 mL) was added [1, 1 '- bis(diphenylphosphino)ferrocene]dichloropalladium (II) (204 mg, 0.24 mmol) at RT. The resultant suspension was stirred for 3 h at 80 °C. The reaction mixture was cooled to RT, diluted with ethyl acetate (100 mL) and washed with water (100 mL) followed by brine (100 mL). The organic layer was concentrated and the residue obtained purified by flash column chromatography to afford 160 mg of the titled product; 1H NMR (300 MHz, CDC13) δ 1.30 (s, 12H), 3.54 (s, 3H), 6.53 (d, J = 9.3 Hz, 1H), 7.60 (d, J = 9.0 Hz, 1H), 7.75 (s, 1H); APCI- MS (m/z) 236 (M+H)+.
Reference: [1] Patent: US2015/111885, 2015, A1, . Location in patent: Paragraph 0574; 0575
[2] Patent: EP2168965, 2010, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2008/8539, 2008, A2, . Location in patent: Page/Page column 117-118
[4] Patent: WO2012/3189, 2012, A1, . Location in patent: Page/Page column 81
[5] Patent: WO2011/60235, 2011, A1, . Location in patent: Page/Page column 22
[6] Patent: WO2015/75665, 2015, A1, . Location in patent: Page/Page column 85; 108
[7] Patent: WO2017/21879, 2017, A1, . Location in patent: Page/Page column 64
[8] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 17, p. 2993 - 2997
  • 2
  • [ 1159607-48-3 ]
  • [ 124-63-0 ]
  • [ 1002309-52-5 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With triethylamine In dichloromethane at 20℃; for 1 h;
Stage #2: With sodium hydroxide In 1,4-dioxane at 70℃; for 1 h;
Example 261B (2.86 g, 10.8 mmol) and triethylamine (6.03 mL, 43.3 mmol) were stirred in dichloromethane (48.1 mL) at ambient temperature. Methanesulfonyl chloride (2.53 mL, 32.4 mmol) was added dropwise and the solution stirred at ambient temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, dioxane (24 mL) and sodium hydroxide (10 percent w/v, 12 mL, 0.427 mmol) were added, and the solution was heated to 70 °C for 1 hour. The solution was neutralized to a pH of 7 with saturated aqueous NH4CI (200 mL). The aqueous phase was extracted with ethyl acetate (3x125 mL). The combined organics were washed with brine, dried (MgSC^), filtered, then concentrated. The residue was purified by flash chromatography (silica gel, 0-25percent ethyl acetate/hexane gradient,) to afford the title compound (2.79 g, 75percent).
Reference: [1] Patent: WO2013/185284, 2013, A1, . Location in patent: Page/Page column 148
  • 3
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
YieldReaction ConditionsOperation in experiment
64% With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide; tricyclohexylphosphine In 1,4-dioxane at 80℃; for 5 h; Inert atmosphere To a mixture of 5-bromo-1-methylpyridin-2(1H)-one (1.0 g, 5.32 mmol), KOH (0.78 g, 7.98 mmol) and bis(pinacolato)diboron (0.162 g, 6.38 mmol) in 1 ,4-dioxane (20 mL), tricyclohexyiphosphine (149 mg, 0.532 mmol), Pd2dba3 (487 mg, 0.532 mmol) were added under N2 atmosphere. The mixture was stirred at about 80 °C for about 5 h. Then water was added, the aqueous layer was extracted with EtOAc (50 mL x 2), and the organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure and the residue was purified by column chromatograph on silica gel to provide ]-methyl-5-(4, 4,5, 5-tetramethyl-], 3, 2-dioxaborolan-2-yl)pyridin-2(]H)-one (0.80 g, 64percent): ‘H NMR (CDC13) 7.70 (s, 1 H), 7.54 (d, J= 8.8 Hz, 1 H), 6.47 (d, J= 8.8 Hz, 1 H), 3.49 (s, 3 H), 1.24(s, 12 H).
Reference: [1] Patent: WO2014/210255, 2014, A1, . Location in patent: Page/Page column 100
  • 4
  • [ 1054483-78-1 ]
  • [ 74-88-4 ]
  • [ 1002309-52-5 ]
Reference: [1] Patent: WO2012/125893, 2012, A1, . Location in patent: Page/Page column 212-213
  • 5
  • [ 445264-61-9 ]
  • [ 74-88-4 ]
  • [ 1002309-52-5 ]
Reference: [1] Patent: WO2008/141119, 2008, A2, . Location in patent: Page/Page column 96-97
  • 6
  • [ 694-85-9 ]
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 21, p. 4745 - 4752
  • 7
  • [ 694-85-9 ]
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 21, p. 4745 - 4752
[2] Synthesis (Germany), 2017, vol. 49, # 21, p. 4745 - 4752
  • 8
  • [ 13466-38-1 ]
  • [ 1002309-52-5 ]
Reference: [1] Patent: WO2014/210255, 2014, A1,
  • 9
  • [ 13466-38-1 ]
  • [ 1002309-52-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 17, p. 2993 - 2997
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