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[ CAS No. 269409-73-6 ] {[proInfo.proName]}

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Chemical Structure| 269409-73-6
Chemical Structure| 269409-73-6
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Product Details of [ 269409-73-6 ]

CAS No. :269409-73-6 MDL No. :MFCD03411930
Formula : C13H17BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :OPWAPCOSDAFWFB-UHFFFAOYSA-N
M.W :248.08 Pubchem ID :2734653
Synonyms :

Calculated chemistry of [ 269409-73-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 69.88
TPSA : 55.76 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) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 1.68
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : 1.25
Consensus Log Po/w : 1.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.02
Solubility : 0.235 mg/ml ; 0.000947 mol/l
Class : Soluble
Log S (Ali) : -3.24
Solubility : 0.142 mg/ml ; 0.00057 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.38
Solubility : 0.104 mg/ml ; 0.000421 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.87

Safety of [ 269409-73-6 ]

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 [ 269409-73-6 ]

* 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 [ 269409-73-6 ]
  • Downstream synthetic route of [ 269409-73-6 ]

[ 269409-73-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 109-04-6 ]
  • [ 269409-73-6 ]
  • [ 4467-07-6 ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In water; N,N-dimethyl-formamide at 110℃; Inert atmosphere To a degassed souton of DMF:H20 (10:1 raUo) (0.3 M), under an atmosphere of nitrogen, was added the pnaco ester (1 mmo), 2-bromopyrdne or 2-choropyrmdne (1 .5 eq.), and Cs2CO3 (4.4 eq.). The whoe mxture was degassed once agan and then Pd(PPh3)4 (5mopercent) was added. The resutng souton was heated to 110°C overnght. The sovent was removed in vacuo to give a dark gummy residue, which was taken up nto EtOAc and H20, then acdfied with 2 M HC to pH 2. The organic ayer was separated and the aqueous ayer was further extracted with EtOAc (2x). The combined organic ayers were dried over MgSO4 and concentrated in vacuo to gve a back ofly residue. The residue was dry oaded ontosWca ge in vacuo then purfied by flash coumn chromatography, eutng with 10-30percent EtOAc/petroeum benzne and 1percent acetic acid to afford the tWe compound.The foHowng compounds were made by Suzuk CoupUng F:P1B1Off white soUd (75percent yed). 1H NMR (400 MHz,DMSO) 6 8.71 8.68 (m, 1 H), 8.67 (s, 1 H), 8.29 (d,J = 7.8 Hz, 1 H), 8.01 (t, J = 8.4 Hz, 2H), 7.91 (td, J =7.8, 1.8 Hz, 1 H), 7.61 (t, J = 7.7 Hz, 1 H), 7.42 7.37(m, 1H). LCMS B rt3.17, m/z200.1 [M + H].
Reference: [1] Patent: WO2016/198507, 2016, A1, . Location in patent: Page/Page column 40; 50
  • 2
  • [ 269409-73-6 ]
  • [ 618-51-9 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 1, p. 140 - 143
  • 3
  • [ 1722-12-9 ]
  • [ 269409-73-6 ]
  • [ 579476-26-9 ]
YieldReaction ConditionsOperation in experiment
79% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In water; N,N-dimethyl-formamide at 110℃; Inert atmosphere To a degassed souton of DMF:H20 (10:1 raUo) (0.3 M), under an atmosphere of nitrogen, was added the pnaco ester (1 mmo), 2-bromopyrdne or 2-choropyrmdne (1 .5 eq.), and Cs2CO3 (4.4 eq.). The whoe mxture was degassed once agan and then Pd(PPh3)4 (5mopercent) was added. The resutng souton was heated to 110°C overnght. The sovent was removed in vacuo to give a dark gummy residue, which was taken up nto EtOAc and H20, then acdfied with 2 M HC to pH 2. The organic ayer was separated and the aqueous ayer was further extracted with EtOAc (2x). The combined organic ayers were dried over MgSO4 and concentrated in vacuo to gve a back ofly residue. The residue was dry oaded ontosWca ge in vacuo then purfied by flash coumn chromatography, eutng with 10-30percent EtOAc/petroeum benzne and 1percent acetic acid to afford the tWe compound.The foHowng compounds were made by Suzuk CoupUng F:CO2HP7BiOff-whte scUd (79percent) yed). 1H NMR (400 MHz,DM80) 6 8.99 (t, J = 1.5 Hz, 1 H), 8.95 (d, J = 4.9Hz, 2H), 8.61 (d, J= 7.9 Hz, 1H), 8.09 (d, J 7.7 Hz,1 H), 7.68 (d, J = 7.8 Hz, 1 H), 7.50 (t, J = 4.9 Hz, 1 H).LCMS B rt2.96 mn, m/z201.1 [M + H].
Reference: [1] Patent: WO2016/198507, 2016, A1, . Location in patent: Page/Page column 40; 51
  • 4
  • [ 269409-73-6 ]
  • [ 380151-86-0 ]
Reference: [1] Chemical Science, 2013, vol. 4, # 3, p. 1111 - 1119
  • 5
  • [ 585-76-2 ]
  • [ 73183-34-3 ]
  • [ 269409-73-6 ]
YieldReaction ConditionsOperation in experiment
89% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; Inert atmosphere To a degassed souDon of 1,4-doxane (0.1 M), under an atmosphere of ntrogen,was addedthe benzoc acid (1 eq.), bs(pnacoato)dthoron (1 .5 eq.), and KOAc (4.4 eq.) sequenUafly.The mixture was degassed once again and then PdC2(dppf) (5 mopercent) was added. Theresutng souUon was heated to 110°C overnight. The sovent was removed in vacuo to givea dark gummy residue, which was taken up nto EtOAc and H20. The organic ayer was separated and the aqueous was further extracted with EtOAc (2x). The combined organic ayers were washed with 2 M HC, dried over MgSO4 and concentrated in vacuo to give a dark brown sohd. The resutng sohd was trtu rated wth petroeum benzne to afford the Uflecompound. The foHowng compounds were made by the 8uzuk couphng method E Bl,Os 0BCO2HFaint brown scUd (89percent). 1H NMR (400 MHz,CDC3) 68.57 (s, 1H), 8.19 (ddd, J= 21.9, 11.8,10.1 Hz, 1 H), 8.09 7.98 (m, 1 H), 7.57 7.38(m, 1H), 1.37 (s, 12H). 13C NMR (101 MHz,CDC3)6 171.66, 139.98, 136.60, 132.84,128.71, 127.93, 84.21, 24.89. LCM8 B rt 3.67mn, m/z249.2 [M + H].
Reference: [1] Patent: WO2016/198507, 2016, A1, . Location in patent: Page/Page column 39; 49
  • 6
  • [ 25015-63-8 ]
  • [ 618-51-9 ]
  • [ 269409-73-6 ]
Reference: [1] Patent: US6680401, 2004, B1, . Location in patent: Page column 20-21
  • 7
  • [ 76-09-5 ]
  • [ 25487-66-5 ]
  • [ 269409-73-6 ]
YieldReaction ConditionsOperation in experiment
91% for 4 h; General procedure: The boronic acids 26 and 27 (0.667 mmol) were dissolved in 6 mL of ethyl acetate and, stirring the solution, pinacol (0.667 mmol) was added. After 4 h the reaction was stopped adding anhydrous Na2SO4 (1 g) and CaCl2 (1 g). The mixture was filtered and concentrated in vacuo (Yields: 91percent of 28 and 89percent of 29).
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 311 - 323
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 16, p. 5012 - 5016
  • 8
  • [ 73183-34-3 ]
  • [ 618-51-9 ]
  • [ 269409-73-6 ]
Reference: [1] Chemical Science, 2016, vol. 7, # 6, p. 3676 - 3680
  • 9
  • [ 99-05-8 ]
  • [ 73183-34-3 ]
  • [ 269409-73-6 ]
Reference: [1] Synlett, 2012, vol. 23, # 9, p. 1394 - 1396
  • 10
  • [ 480425-35-2 ]
  • [ 269409-73-6 ]
Reference: [1] Synthesis (Germany), 2012, vol. 44, # 14, p. 2173 - 2180
  • 11
  • [ 73183-34-3 ]
  • [ 269409-73-6 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 14 - 24
  • 12
  • [ 99-05-8 ]
  • [ 269409-73-6 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
[2] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 14 - 24
  • 13
  • [ 618-89-3 ]
  • [ 73183-34-3 ]
  • [ 269409-73-6 ]
Reference: [1] Synthesis (Germany), 2012, vol. 44, # 14, p. 2173 - 2180
  • 14
  • [ 4595-59-9 ]
  • [ 269409-73-6 ]
  • [ 852180-74-6 ]
YieldReaction ConditionsOperation in experiment
45% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,4-dioxane; water at 95℃; Inert atmosphere General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 °C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.
34% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 120℃; for 0.5 h; Inert atmosphere; Microwave irradiation 3-(4.4,5.5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzoic acid (496 mg, 2.00 mmol), 5- bromopyrimidine (382 mg, 2.40 mmol), PdC (dppf) DCM complex (82 mg, 5 molpercent) were stirred in 1 ,4-dioxane (10 mL) under nitrogen and a solution of potassium carbonate (829 mg, 6.00 mmol) in water (5 mL) was added. The mixture was degassed with a stream of nitrogen bubbles and heated in the microwave (120 C/30 minutes). The volatiles were removed in vacuo and the aqueous residue diluted with water (50 mL) and DCM (50 mL). The mixture was filtered through celite, the DCM phase discarded and the aqueous phase extracted with further DCM (2 50 mL). The DCM extracts were again discarded, the aqueous phase was adjusted to pH 3 with 30percent w/v aqueous NaHSCU and the precipitate collected by filtration and dried under vacuum (40 C/3 hours over P2O5) to give the desired compound (137 mg, 34percent yield) as a grey solid. LCMS-B: RT 3.25 min; m/z 201.1 [M+H]+
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 634 - 648
[2] Patent: WO2016/34673, 2016, A1, . Location in patent: Page/Page column 80
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