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[ CAS No. 1054483-78-1 ] {[proInfo.proName]}

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Chemical Structure| 1054483-78-1
Chemical Structure| 1054483-78-1
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Product Details of [ 1054483-78-1 ]

CAS No. :1054483-78-1 MDL No. :MFCD06795671
Formula : C11H16BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WAUWXCUPDOXYKS-UHFFFAOYSA-N
M.W : 221.06 Pubchem ID :17750253
Synonyms :

Calculated chemistry of [ 1054483-78-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.55
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.74
TPSA : 51.58 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) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.41
Log Po/w (SILICOS-IT) : 0.82
Consensus Log Po/w : 0.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.57
Solubility : 0.597 mg/ml ; 0.0027 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.663 mg/ml ; 0.003 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.194 mg/ml ; 0.000879 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 1054483-78-1 ]

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 [ 1054483-78-1 ]

* 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 [ 1054483-78-1 ]
  • Downstream synthetic route of [ 1054483-78-1 ]

[ 1054483-78-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 109-04-6 ]
  • [ 1054483-78-1 ]
  • [ 381233-78-9 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 75℃; Finally, several additional analogues designed to evaluate replacement of the pyridazine in 1 with phenyl and pyridyl moieties, were prepared using the methodology outlined in Scheme 3. Suzuki coupling of 2-bromopyridine (18) with various boronic acids afforded 19 and 20 (Ghiron et al, J. Med. Chem. 2010, 53, 4379). Treatment of 20 with P2S5 in pyridine at 120 °C provided 21 in 71percent yield. Alkylation of 21 with 2- methylbenzyl bromide in the presence of K2C03 in DMF generated 22. Scheme 3. Reagents and conditions: (a) Pd(PPh3)4, Na2C03, CH3CN/H20 (1/1), 75 °C, 4- benzylthiophenylboronic acid (54percent); (b) Pd(PPh3)4, Na2C03, CH3CN/H20 (1/1), 75 °C, 6-hydroxypyridine-3-boronic acid pinacol ester (70percent>); (c) P2S5, pyridine, 120 °C (71percent>); (d) 2-methylbenzyl bromide, K2C03, DMF (76percent).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5774 - 5777
[2] Patent: WO2013/19938, 2013, A1, . Location in patent: Page/Page column 34; 35
  • 2
  • [ 1054483-78-1 ]
  • [ 74-88-4 ]
  • [ 1002309-52-5 ]
Reference: [1] Patent: WO2012/125893, 2012, A1, . Location in patent: Page/Page column 212-213
  • 3
  • [ 13466-38-1 ]
  • [ 73183-34-3 ]
  • [ 1054483-78-1 ]
YieldReaction ConditionsOperation in experiment
64% With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine In 1,4-dioxane at 110℃; Sealed tube A solution of 5-bromopyridin-2-ol SM1 (0.1 g, 0.57 mmol), 4,4,4,4,5,5,5,5-octamethyl- 2,2-bi(1,3,2-dioxaborolane) SM2 (0.88 g, 3.45 mmol), Tricyclohexyl phosphine (0.032 g, 0.114mmol), Pd2(dba)3 (0.052 g, 0.057 mmol) and KOAc (0.17 g, 1.71 mmol) dissolved with dioxane (10 mL) in sealed tube was stirred at 110 °C overnight. After consumption of the starting material (by LC-MS), the solvent from reaction mixture was removed under reduced pressure, the residue was diluted with brine and extracted with EtOAc. Combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain cmde product, which waspurified by silica gel column chromatography to afford compound 3 (0.08 g, 64percent) as a black liquid.TLC: 50percent EA/PE.
Reference: [1] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 644
  • 4
  • [ 1054483-78-1 ]
  • [ 1895-39-2 ]
  • [ 1333222-12-0 ]
YieldReaction ConditionsOperation in experiment
53% at 80℃; Sealed tube In a sealed tube was added 2-hydroxy-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (300 mg, 1.357 mmol), sodium chlorodifluoroacetate (320 mg, 2.036 mmol) in acetonitrile (5 mL). This suspension was heated to 80°C and stirred overnight. The reaction mixture was cooled down to rt, diluted with EtOAc, washed with an aqueous solution of NaHC03 and brine. The organic layer dried over MgS04, filtered and evaporated. Purification by flash chromatography on silica gel (CH2CI2/MeOH, 95/5) gave the title compound (197 mg, 53percent yield). MS: 272.8 [M+H]+, Rt (6) = 3.12 min.
53% at 80℃; Sealed tube 2-Difluoromethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine
In a sealed tube was added 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (300 mg, 1.357 mmol), sodium chlorodifluoroacetate (320 mg, 2.036 mmol) in acetonitrile (5 mL).
This suspension was heated to 80° C. and stirred overnight.
The reaction mixture was cooled down to rt, diluted with EtOAc, washed with an aqueous solution of NaHCO3 and brine.
The organic layer dried over MgSO4, filtered and evaporated.
Purification by flash chromatography on silica gel (CH2Cl2/MeOH, 95/5) gave the title compound (197 mg, 53percent yield). MS: 272.8 [M+H]+, Rt(6)=3.12 min.
Reference: [1] Patent: WO2013/57711, 2013, A1, . Location in patent: Page/Page column 49
[2] Patent: US2015/342951, 2015, A1, . Location in patent: Paragraph 0859-0860
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