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[ CAS No. 862723-42-0 ] {[proInfo.proName]}

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Chemical Structure| 862723-42-0
Chemical Structure| 862723-42-0
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Product Details of [ 862723-42-0 ]

CAS No. :862723-42-0 MDL No. :MFCD07367523
Formula : C13H17BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SAGPUUKLGWNGOS-UHFFFAOYSA-N
M.W : 244.10 Pubchem ID :17750469
Synonyms :

Calculated chemistry of [ 862723-42-0 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.46
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.57
TPSA : 47.14 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.54
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.19
Log Po/w (SILICOS-IT) : 1.88
Consensus Log Po/w : 1.49

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.26
Solubility : 0.135 mg/ml ; 0.000553 mol/l
Class : Soluble
Log S (Ali) : -3.18
Solubility : 0.162 mg/ml ; 0.000665 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.52
Solubility : 0.00744 mg/ml ; 0.0000305 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.85

Safety of [ 862723-42-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 862723-42-0 ]

* 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 [ 862723-42-0 ]
  • Downstream synthetic route of [ 862723-42-0 ]

[ 862723-42-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 53857-57-1 ]
  • [ 73183-34-3 ]
  • [ 862723-42-0 ]
YieldReaction ConditionsOperation in experiment
84% With potassium acetate In N,N-dimethyl-formamide at 90℃; for 24 h; Example 9; 545-r(iiS.5iS)-6-methyl-3.6-diazabi(^clor3.2.01heptan-3-yl1pyridin-3-vU-liy-indazole bistrifluoroacetateExample 9A 5-("4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-ylVlH-indazole5-bromo-lH-indazole (US2003199511, 9.45 g, 48 mmol,) was coupled with bis(pinacolato)diboron (Combi-Blocks, 15.5g, 61 mmol) under the catalysis of Pd(dppf)2Cl2*Cη2Cl2 (Aldrich, 985 mg, 1.2 mmol) in the presence of KOAc (Aldrich, 16.7 g, 170 mmol) in dry DMF (160 ml) at 900C for 24 hours. After the reaction was completed, it was cooled to ambient temperature, diluted with EtOAc (250 mL) and washed with water (2 x 50 mL). The organic phase was concentrated under reduced pressure, and the residue was purified with chromatography (SiO2, Hexane:EtOAc (v. 10:1), Rf=O.6) to give the title compound (9.8 g, yield, 84percent). 1H NMR (300 MHz, CD3OD) δ ppm 1.36 (s, 12 H) 7.51 (dt, J=8.5, 1.0 Hz, 1 H) 7.73 (dd, J=8.5, 1.0 Hz, 1 H) 8.08 (d, J=1.0 Hz, 1 H) 8.23 (t, J=1.0 Hz, 1 H); MS (DCI/NH3) m/z 245 (M+ 1)+.
81% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 24 h; Inert atmosphere The A13-1 (300mg, 1.52mmol) was dissolved in DMSO (10mL), was added bis (pinacolato) borate (570mg, 2.24mmol), KOAc(440mg, 4.49mmol), Pd (dppf) 2Cl2 (60mg, 0.073mmol), purged with nitrogen, 90 stirred for 24 hours, cooled to room temperature, siliconDiatomaceous earth filtration, the filtrate was diluted with ethyl acetate (20 mL), saturated brine (20mL × 3), dried over anhydrous sodium sulfate, and sodium sulfate was filtered, spin-dry the solvent,The residue was purified by column chromatography (dichloromethane to dichloromethane: methanol = 100: 1) to give a brown oil (300mg, 81percent).
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen flow 5-bromo-1H-indazole (25.22 g, 0.128 mol), 4,4,4 ',4',5,5,5 ',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (48.58 g, 0.191 mol), Pd(dppf)Cl2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) and the mixture at 130°C, It was stirred for 12 hours. After the reaction was terminated by the removal of water and then extracted with ethyl acetate and MgSO4, purified by column chromatography (Hexane: EA = 10: 1 (v / v)) purified 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.49 g, a yield of 72percent).
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen flow 5-bromo-1H-indazole (25.22 g, 0.128 mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi (1,3 ,2-dioxaborolane) (48.58 g, 0.191 mol), Pd (dppf) Cl2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) and then, the mixture at 130 °C was stirred for 12 hours. After completion of the reaction, the reaction extracted with ethyl acetate, and purified by the removal of water with MgSO4 and column chromatography (Hexane: EA = 10: 1 (v / v)) to give 5- (4,4,5 a, 5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indazole (22.49 g, yield: to obtain a 72percent).
72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 130℃; for 12 h; Inert atmosphere Under a nitrogen flow 5-bromo-1H-indazole (25.22 g, 0.128 mol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3 ,2-dioxaborolane) (48.58 g, 0.191 mol), Pd (dppf) Cl2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and 1,4-dioxane (500 ml) and the mixture 130? in It was stirred for 12 hours.After the reaction was terminated by the removal of water and then extracted with ethyl acetate and MgSO4, purified by column chromatography (Hexane: EA = 10: 1 (v / v)) purified 5- (4,4,5,5-tetramethyl- by a 1,3,2-dioxaborolan-2-yl) -1H-indazole (22.49 g, a yield of 72percent).
1 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere To a solution of 5-bromoindazole (1.97 g, 10 mmol) in 1,4-dioxane (50 mL) was added bis(pinacolato)diboron (2.67 g, 10.5 mmol), l,l-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.82 g, 1 mmol), and potassium acetate (2.0 g, 20 mmol). The resulting mixture was degassed and then stirred overnight at 80 °C under an Ar atmosphere. After the reaction was completed as monitored by LC-MS, the mixture was diluted with water (200 mL) and then extracted with EtOAc. The combined organic layers were washed with water and brine, and then dried. The solvent was concentrated and the residue was purified by column chromatography (EtOAc / Pet = 1 : 1) to give indazole-5-boronic acid pinacol ester (1.0 g)

Reference: [1] Patent: WO2009/67586, 2009, A1, . Location in patent: Page/Page column 42
[2] Patent: CN105254613, 2016, A, . Location in patent: Paragraph 0125; 0126; 0127
[3] Patent: KR2015/88007, 2015, A, . Location in patent: Paragraph 0282; 0283; 0284
[4] Patent: KR101561332, 2015, B1, . Location in patent: Paragraph 0117-0121
[5] Patent: KR101612160, 2016, B1, . Location in patent: Paragraph 0114; 0115; 0116; 0117; 0118
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3856 - 3873
[7] Patent: US2008/45539, 2008, A1, . Location in patent: Page/Page column 16
[8] Patent: WO2010/59788, 2010, A1, . Location in patent: Page/Page column 55
[9] Patent: US2007/203143, 2007, A1, . Location in patent: Page/Page column 57-58
[10] Patent: US2011/82138, 2011, A1, . Location in patent: Page/Page column 23
[11] Patent: WO2014/90692, 2014, A1, . Location in patent: Page/Page column 66
[12] Patent: WO2015/140717, 2015, A1, . Location in patent: Page/Page column 92; 93
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