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[ CAS No. 1040377-02-3 ] {[proInfo.proName]}

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Chemical Structure| 1040377-02-3
Chemical Structure| 1040377-02-3
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Product Details of [ 1040377-02-3 ]

CAS No. :1040377-02-3 MDL No. :MFCD11505042
Formula : C8H11BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :WRDSDCYKWVXMRY-UHFFFAOYSA-N
M.W : 231.09 Pubchem ID :51063926
Synonyms :

Calculated chemistry of [ 1040377-02-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.62
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.39
TPSA : 27.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 1.23
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : 1.73
Consensus Log Po/w : 1.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.29
Solubility : 1.19 mg/ml ; 0.00513 mol/l
Class : Soluble
Log S (Ali) : -1.4
Solubility : 9.29 mg/ml ; 0.0402 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.17
Solubility : 1.57 mg/ml ; 0.00681 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 1040377-02-3 ]

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 [ 1040377-02-3 ]

* 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 [ 1040377-02-3 ]
  • Downstream synthetic route of [ 1040377-02-3 ]

[ 1040377-02-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1040377-02-3 ]
  • [ 73183-34-3 ]
  • [ 1003846-21-6 ]
Reference: [1] Patent: WO2014/86032, 2014, A1, . Location in patent: Page/Page column 43
  • 2
  • [ 1040377-02-3 ]
  • [ 73183-34-3 ]
  • [ 1040377-03-4 ]
YieldReaction ConditionsOperation in experiment
68% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 10 h; Inert atmosphere To a solution of 4-bromo-1-(oxan-4-yl)-1H-pyrazole (1.0 g, 4.33 mmol) and 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane 38 (1.32 g, 5.19 mmol) in 10 ml of DMF was added potassium acetate (1.27 g, 12.98 mmol), followed by 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (177 mg, 0.22 mmol) under argon. The resulting mixture was stirred at 80 0C for 10 h and then diluted with 40 ml of water. The mixture was extracted with EA (30 ml × 3). The combined organic phase was washed with water (30 ml × 3), brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography (EA/PE, 1/4) to afford 39 as a white solid in 68percent yield. NMR (300 MHz, CDCl3) δ 7.80 (s, 1H), 7.75 (s, 1H), 4.42-4.31 (m, 1H), 4.12-4.07 (m, 2H), 3.57-3.49 (m, 2H), 2.13-1.99 (m, 4H), 1.32 (s, 12H).
68% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 80℃; for 10 h; Inert atmosphere To a solution of 4-bromo-1-(oxan-4-yl)-1H-pyrazole 26a (1.00 g, 4.33 mmol) and 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.32 g, 5.19 mmol) in 10 mL of DMF was added potassium acetate (1.27 g, 12.98 mmol), followed by 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (177 mg, 0.22 mmol) under argon. The resulting mixture was stirred at 80 °C for 10 h and then diluted with 40 mL of water. The mixture was extracted with EA (3 × 30 mL). The combined organic phase was washed with water (3 × 30 mL), brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography (EA/PE, 1:4) to afford 25c as white solid in 68percent yield. 1H NMR (300 MHz, CDCl3) δ 7.80 (s, 1H), 7.75 (s, 1H), 4.42-4.31 (m, 1H), 4.12-4.07 (m, 2H), 3.57-3.49 (m, 2H), 2.13-1.99 (m, 4H), 1.32 (s, 12H).
19% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 90℃; C. To a solution of 4-bromo-l-(tetrahydro-2H-pyran-4-yl)-lH- pyrazole (2.90 g, 12.6 mmol) in dimethyl sulfoxide (25 mL) was added potassium acetate (4.94 g, 50.4 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l,3,2-dioxaborolane (6.40 g, 25.2 mmol). The mixture was degassed for 10 min, and then [l, -bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.922 g, 1.26 mmol) was added. The mixture was degassed for another 10 minutes and heated at 90 °C overnight, diluted with ethyl acetate (80 mL), washed with water (2 x 20 mL), brine (20 mL), dried and filtered. The solvent of the filtrate was removed and the residue was purified by flash column chromatography eluted with 20percent ethyl acetate in hexanes to afford l-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-pyrazole (0.66 g, 19percent) as a white solid. 1H NMR (400 Hz, CDCls) δ 7.81 (s, 1H), 7.76 (s, 1H), 4.42-4.32 (m, 1H), 4.14-4.06 (m, 2H), 3.58-3.50 (m, 2H), 2.16-1.98 (m, 4H), 1.32 (s, 12H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 17, p. 5169 - 5180
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6804 - 6820
[3] Patent: WO2015/81257, 2015, A2, . Location in patent: Page/Page column 84-85
[4] Patent: WO2011/79804, 2011, A1, . Location in patent: Page/Page column 41
[5] Patent: US2012/245178, 2012, A1, . Location in patent: Page/Page column 25
[6] Patent: WO2009/87212, 2009, A2, . Location in patent: Page/Page column 145-146
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