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[ CAS No. 845306-08-3 ] {[proInfo.proName]}

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Chemical Structure| 845306-08-3
Chemical Structure| 845306-08-3
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Product Details of [ 845306-08-3 ]

CAS No. :845306-08-3 MDL No. :MFCD08436052
Formula : C10H12BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GBAJDPJECJPPSP-UHFFFAOYSA-N
M.W : 258.11 Pubchem ID :24997839
Synonyms :

Calculated chemistry of [ 845306-08-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.68
TPSA : 39.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.54
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.8
Log Po/w (MLOGP) : 1.98
Log Po/w (SILICOS-IT) : 2.58
Consensus Log Po/w : 2.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.27
Solubility : 0.14 mg/ml ; 0.000541 mol/l
Class : Soluble
Log S (Ali) : -3.19
Solubility : 0.168 mg/ml ; 0.000651 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.0428 mg/ml ; 0.000166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.0

Safety of [ 845306-08-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 845306-08-3 ]

* 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 [ 845306-08-3 ]
  • Downstream synthetic route of [ 845306-08-3 ]

[ 845306-08-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 845306-08-3 ]
  • [ 30766-11-1 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 17, p. 2244 - 2246
  • 2
  • [ 30766-11-1 ]
  • [ 75-65-0 ]
  • [ 845306-08-3 ]
YieldReaction ConditionsOperation in experiment
73% at 20 - 40℃; for 2.16667 h; para-Toluene sulfonyl chloride (262mg, 1.38mmol) was added to a solution of 5-bromo-2-carboxypyridine (118mg, 0.58mmol) and pyridine (0.3mL, 0.39mmol) intert-butanol (1mL) and the mixture was stirred at 40°C for 10 minutes and room temperature for 2 hours.
Saturated sodium hydrogen carbonate solution (4mL) was then added and the mixture was stirred for 5 minutes.
Diethyl ether was next added and the bi-phasic mixture was stirred for a further 10 minutes.
The organic layer was then separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo.
Purification of the residue by column chromatography on silica gel, eluding with pentane:ethyl acetate, 100:0 to 80:20, afforded the title compound as a colourless solid in 73percent yield, 110mg.
1H-NMR(CDCl3, 400MHz) δ: 1.65(s, 9H), 7.95(m, 2H), 8.88(m, 1H)
MS ES+ m/z 539 [M2Na]+
Reference: [1] Patent: EP1595881, 2005, A1, . Location in patent: Page/Page column 62
[2] Patent: WO2005/14571, 2005, A1, . Location in patent: Page/Page column 27
[3] Patent: WO2006/29906, 2006, A1, . Location in patent: Page/Page column 16-17
[4] Patent: WO2012/143599, 2012, A1, . Location in patent: Page/Page column 47-48
  • 3
  • [ 29682-15-3 ]
  • [ 75-65-0 ]
  • [ 845306-08-3 ]
Reference: [1] Organic Letters, 2008, vol. 10, # 13, p. 2909 - 2912
  • 4
  • [ 30766-11-1 ]
  • [ 845306-08-3 ]
Reference: [1] Patent: US2014/94474, 2014, A1, . Location in patent: Page/Page column
  • 5
  • [ 30766-11-1 ]
  • [ 36805-97-7 ]
  • [ 845306-08-3 ]
Reference: [1] Patent: WO2015/161011, 2015, A1, . Location in patent: Page/Page column 103
  • 6
  • [ 845306-08-3 ]
  • [ 1158763-55-3 ]
Reference: [1] Patent: WO2012/3189, 2012, A1,
  • 7
  • [ 845306-08-3 ]
  • [ 73183-34-3 ]
  • [ 1354356-24-3 ]
YieldReaction ConditionsOperation in experiment
100% With potassium acetate In 1,4-dioxane; dimethyl sulfoxide at 90℃; for 3 h; Inert atmosphere Example 192 4-((3 S,4S)- 1 -( 1 -cyanocyclopropanecarbonyl)-4-methylpyrrolidin-3 -ylamino)-6-(6- (dimethylcarbamoyl)pyridin-3-yl)pyrrolo[l,2-b]pyridazine-3-Step 1; tert-butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)picolinate [00357] A reaction vial was charged with tert-butyl 5-bromopicolinate (0.50 g, 1.937 mmol), potassium acetate (0.380 g, 3.87 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'- bi(l,3,2-dioxaborolane) (0.590 g, 2.325 mmol) in dioxane (3.69 mL) and DMSO (0.184 mL). The resulting mixture was sparged with argon for ~ 5 min. then PdCl2(dppf)-CH2Cl2 adduct (0.079 g, 0.097 mmol) was added and the resulting mixture was heated at 90 °C for 3h. After cooling to rt, the mixture was partitioned between EtOAc (300 mL) and water (80 mL) and the layers were separated. The organic portion was washed with water (100 mL x 2), brine, then dried over MgS04, filtered and concentrated to afford dark oil as the crude product mixture. This material was purified via ISCO columnchromatography (Hex/EtOAc; 24g silica column) to afford after isoaltion andconcentration of the desired fractions 0.60 g (~ quant.) of a near white solid as the title compound. HPLC (method B) retention time = 2.07 min. XH NMR (400MHz,CHLOROFORM-d) δ 9.05 (s, IH), 8.17 (dd, J=7.8, 1.7 Hz, IH), 7.99 (dd, J=7.7, 0.9 Hz, IH), 1.28 (s, 9H), 1.25 (s, 12H).
Reference: [1] Patent: WO2012/125893, 2012, A1, . Location in patent: Page/Page column 225-226
[2] Patent: WO2012/3189, 2012, A1, . Location in patent: Page/Page column 112
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