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[ CAS No. 445264-61-9 ] {[proInfo.proName]}

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Chemical Structure| 445264-61-9
Chemical Structure| 445264-61-9
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Product Details of [ 445264-61-9 ]

CAS No. :445264-61-9 MDL No. :MFCD05663858
Formula : C12H18BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QOGNDJLSYMJGPP-UHFFFAOYSA-N
M.W :235.09 Pubchem ID :16217714
Synonyms :

Calculated chemistry of [ 445264-61-9 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.58
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 67.2
TPSA : 40.58 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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 1.39
Log Po/w (MLOGP) : 0.69
Log Po/w (SILICOS-IT) : 1.32
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.395 mg/ml ; 0.00168 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.559 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.76
Solubility : 0.0409 mg/ml ; 0.000174 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.94

Safety of [ 445264-61-9 ]

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

Application In Synthesis of [ 445264-61-9 ]

* 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 [ 445264-61-9 ]
  • Downstream synthetic route of [ 445264-61-9 ]

[ 445264-61-9 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 445264-61-9 ]
  • [ 51834-97-0 ]
YieldReaction ConditionsOperation in experiment
2.4 g With sodium perborate tetrahydrate In tetrahydrofuran; water at 20℃; for 2 h; To a stirred suspension of sodium perborate tetrahydrate (6.87 g, 44.68 mmol) in water was added 2-methoxy-5 -(4,4,5,5 -tetramethyl-[ 1,3,2] dioxaborolan-2-yl)-pyridine (3.5 g, 14.68 mmol) in THF (70 mL) at room temperature. The resulting reaction mixture was stirred for 2 hr at room temperature. The reaction mass was extracted with ethyl acetate (200 mL), washed with brine dried over Na2SO4 and concentrated under reduced pressure to provide the crude which was purified by silica gel (100-200 mesh) column chromatography using 20percent EtOAc in hexane as eluent to afford 2.4 g of 6-methoxy-pyridin-3-ol. LCMS: 126 (M+H).
Reference: [1] Patent: WO2014/186035, 2014, A1, . Location in patent: Page/Page column 151
  • 2
  • [ 445264-61-9 ]
  • [ 76053-45-7 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 45, p. 8624 - 8635
  • 3
  • [ 1628-89-3 ]
  • [ 73183-34-3 ]
  • [ 445264-61-9 ]
  • [ 408502-23-8 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4133 - 4136
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327
[3] Patent: US2015/65743, 2015, A1, . Location in patent: Paragraph 0372; 0373
[4] Patent: WO2015/89119, 2015, A1, . Location in patent: Page/Page column 34
  • 4
  • [ 1628-89-3 ]
  • [ 73183-34-3 ]
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  • [ 408502-23-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327
  • 5
  • [ 13472-85-0 ]
  • [ 73183-34-3 ]
  • [ 445264-61-9 ]
YieldReaction ConditionsOperation in experiment
84% With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 108℃; Inert atmosphere Step j:
2-methoxy-5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Compound R-3-2)
A mixture of compound 303 (55 g, 0.29 mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (90 g, 0.35 mol), potassium acetate (57 g, 0.58 mol) and bis(triphenylphosphine)palladium(II) chloride (2.2 g, 3 mmol) in anhydrous dioxane (500 mL) was heated at 108° C. under N2 atmosphere overnight.
The reaction mixture was concentrated and purified by column chromatography eluted with hexanes/ethyl acetate to afford title compound R-3-2 (58 g, 84percent).
84% With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 108℃; Inert atmosphere A mixture of compound 303 (55 g, 0.29 mol), 4,4,4’,4’,5,5,5’,5’-octamethyl -2,2’- bi(1,3,2-dioxaborolane) (90 g, 0.35 mol), potassium acetate (57 g, 0.58 mol) and bis(triphenylphosphine)palladium(II) chloride (2.2 g, 3 mmol) in anhydrous dioxane (500 mL) was heated at 108°C under N2 atmosphere overnight. The reaction mixture wasconcentrated and purified by column chromatography eluted with hexanes/ethyl acetate to afford title compound R-3-2 (58 g, 84 percent). ‘H NMR (400 MHz, DMSO-d6): ö 1.30 (s, 12H), 3.88 (s, 3H), 6.81 (d, J= 8.0 Hz, 1H), 7.88 (dd, J 8.0 Hz, 2.0Hz, 1H), 8.41 (d, J2.0Hz, 1H).
3.6 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In toluene for 2 h; Inert atmosphere; Reflux 5-Bromo-2-methoxypyridine (5g, 26.59 mmol), bis(pinacolato)diborane (10.13 g, 39.89 mmol) and potassium acetate (10.44 g, 106 mmol) were taken in dry toluene (60 mL) and degassed with nitrogen for 20 mi Pd(dppf)C12.DCM (2.17 g, 2.66 mmol) was added to the reaction under nitrogen atmosphere and the resulting mixture was refluxed for 2 hr. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to 25°C and filtered through a Celite® reagent pad. Filtrate was diluted with ethyl acetate (200 mL), washed with water followed by brine, dried over Na2SO4 and concentrated under reduced pressure to provide the crude which was purified by silica gel (100-200 mesh) column chromatography using 10percent EtOAc in hexane as eluent to afford 3.6 g of 2-methoxy-5 -(4,4,5,5 -tetramethyl- [1,3 ,2]dioxaborolan-2-yl)- pyridine.
Reference: [1] Patent: US9249156, 2016, B2, . Location in patent: Page/Page column 36
[2] Patent: WO2018/85342, 2018, A1, . Location in patent: Page/Page column 26; 28
[3] Patent: WO2014/186035, 2014, A1, . Location in patent: Page/Page column 151
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2496 - 2500
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6477 - 6485
[6] Patent: CN105906557, 2016, A, . Location in patent: Paragraph 0005; 0014
  • 6
  • [ 61676-62-8 ]
  • [ 445264-61-9 ]
YieldReaction ConditionsOperation in experiment
67.5%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at 20℃; for 1 h;
To a solution of 5-bromo-2-methoxy-pyridine (1.453 g, 7.73 mmol) in THF (50 mL) at -78° C. under N2 was added n-BuLi (3.4 mL, 2.5 M in hexanes, 8.5 mmol) dropwise. The mixture was stirred at -78° C. for 30 minutes, then 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.4 mL, 11.60 mmol) was added. The reaction mixture was warmed to room temperature for 1 hour, then poured into water and extracted with EtOAc. The combined extracts were washed with water and brine, dried (MgSO4), filtered and concentrated to give 2A (1.221 g, 67.5percent) as a colorless oil.
Reference: [1] Patent: US2005/192310, 2005, A1, . Location in patent: Page/Page column 21
  • 7
  • [ 1628-89-3 ]
  • [ 73183-34-3 ]
  • [ 445264-61-9 ]
  • [ 408502-23-8 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4133 - 4136
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327
[3] Patent: US2015/65743, 2015, A1, . Location in patent: Paragraph 0372; 0373
[4] Patent: WO2015/89119, 2015, A1, . Location in patent: Page/Page column 34
  • 8
  • [ 13472-85-0 ]
  • [ 61676-62-8 ]
  • [ 445264-61-9 ]
Reference: [1] Synthesis, 2012, vol. 44, # 5, p. 735 - 746
[2] Synlett, 2009, # 15, p. 2508 - 2512
  • 9
  • [ 6628-77-9 ]
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933
  • 10
  • [ 1628-89-3 ]
  • [ 445264-61-9 ]
Reference: [1] Synthesis, 2012, vol. 44, # 5, p. 735 - 746
[2] Patent: WO2014/186035, 2014, A1,
[3] Patent: US9249156, 2016, B2,
[4] Patent: WO2018/85342, 2018, A1,
  • 11
  • [ 1628-89-3 ]
  • [ 73183-34-3 ]
  • [ 445264-61-9 ]
  • [ 408502-23-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327
  • 12
  • [ 445264-61-9 ]
  • [ 74-88-4 ]
  • [ 1002309-52-5 ]
Reference: [1] Patent: WO2008/141119, 2008, A2, . Location in patent: Page/Page column 96-97
  • 13
  • [ 445264-61-9 ]
  • [ 1339928-25-4 ]
Reference: [1] Patent: US9249156, 2016, B2,
[2] Patent: WO2018/85342, 2018, A1,
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