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[ CAS No. 943994-02-3 ] {[proInfo.proName]}

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Chemical Structure| 943994-02-3
Chemical Structure| 943994-02-3
Structure of 943994-02-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 943994-02-3 ]

CAS No. :943994-02-3 MDL No. :MFCD12755796
Formula : C14H18BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZXOSNHPLTJAXSA-UHFFFAOYSA-N
M.W : 275.11 Pubchem ID :46856474
Synonyms :

Calculated chemistry of [ 943994-02-3 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 79.74
TPSA : 56.79 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) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 0.75
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 0.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.368 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (Ali) : -2.67
Solubility : 0.583 mg/ml ; 0.00212 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.23
Solubility : 0.0163 mg/ml ; 0.0000593 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.01

Safety of [ 943994-02-3 ]

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 [ 943994-02-3 ]

* 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 [ 943994-02-3 ]
  • Downstream synthetic route of [ 943994-02-3 ]

[ 943994-02-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 24036-52-0 ]
  • [ 73183-34-3 ]
  • [ 943994-02-3 ]
YieldReaction ConditionsOperation in experiment
69% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Inert atmosphere To the solution of XXXV-2 (2.3 g, 10 mmol) in dioxane (20 mL), bis (pinacolato)diboron (3.05 g, 12 mmol), potassium acetate (2 g , 20 mmol) and Pd(dppf)C12 (730 mg, 1 mmol) was added. The mixture was purged with nitrogen and sitiffed at 90°C overnight. Then the mixture was diluted with EA (200 mL) and filtrated. The organic phase was washed with brine, dried over Na2SO4, concentrated in vacuo to give the crude product. The residue was purification by column chromatography on silica gel (PE:EA=3: ito 1:1) to give XXXV-4 (1.9 g, 69percent yield)
56% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 24 h; Inert atmosphere A solution of the compound 4a (3.33g, 14.67mmol), 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolane) (4.48g, 17.61mmol), potassium acetate (2.88g, 29.34mmol), Pd (dppf) Cl2 (0.15g, 0.20mmol) in dioxane (40mL) was heated to 100 °Cunder N2 for 24 hours. The reaction mixture was filtered and concentrated under reduced pressure, the residue was purified by column chromatography to afford the compound 5a (2.25g, 56percent). MS: 276 (M+H) +.
55% at 100℃; for 16 h; Inert atmosphere Preparation 13: 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-ylboronic acid; Step 1 : 6-(4,4,5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)-2H-benzorbiπ.41oxazin-3(4H)- one; A mixture of 6-Bromo-4H-benzo[1 ,4]oxazin-3-one (100 mg, 0.439 mmol), 4,4,5,5,4I,4I,5l,5I-Octamethyl-[2,2']bi[[1 ,3,2]dioxaborolanyl] (123 mg, 0.483 mmol), potassium acetate (159 mg, 1.54 mmol), 1 ,1-bis(diphenylphosphino)ferrocene (12.2 mg, 0.022 mmol) in dioxane (4 ml_). The mixture was degassed with nitrogen for approximately 20 minutes. [1 ,1-bis(diphenylphosphino) ferrocene]dichloropalladium (II) (18.0 mg, 0.220 mmol) was added followed by additional 5 minutes of degassing. The mixture was heated to 100°C for 16 h. The reaction mixture was cooled to room temperature, filtered through celite and concentrated. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography eluting with a gradient of 25percent-50percent ethyl acetate/ heptane. The title compound was obtained as a white solid (66 mg, 55percent). 1 H NMR (400 MHz, METHANOL-^) δ ppm 1.33 (12 H, s), 4.60 (2 H, s), 6.93 (1 H, d, J=8.3 Hz), 7.26 (1 H, s), 7.36 (1 H, d, J=I.9 Hz).
320 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 4 h; Inert atmosphere 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (275 mg, 1.21 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (466 mg, 1.84 mmol), potassium acetate (184 mg, 1.87 mmol), and Dichloro 1,1-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane (47 mg, 0.06 mmol) were added to a flask and container was evacuated and backfilled with argon. Reagents were taken up in dioxane (9 mL) and system was again purged with argon. Mixture was then heated at 100° C. for 4 hours. After cooling to rt, reaction mixture was filtered over celite, washing with ethyl acetate. Filtrate was concentrated under reduced pressure and resulting reside was purified by silica gel column chromatography (0-40percent ethyl acetate/hexanes) to yield 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one 7.17 (320 mg).

Reference: [1] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0937
[2] Patent: WO2017/211303, 2017, A1, . Location in patent: Page/Page column 36
[3] Patent: WO2010/116282, 2010, A1, . Location in patent: Page/Page column 55-56
[4] Patent: WO2007/77961, 2007, A2, . Location in patent: Page/Page column 227
[5] Patent: KR2016/37198, 2016, A, . Location in patent: Paragraph 3281-3283
  • 2
  • [ 40925-68-6 ]
  • [ 943994-02-3 ]
Reference: [1] Patent: WO2015/153683, 2015, A1,
[2] Patent: WO2017/211303, 2017, A1,
  • 3
  • [ 943994-02-3 ]
  • [ 1246765-28-5 ]
YieldReaction ConditionsOperation in experiment
66% With hydrogenchloride; water In acetonitrile at 20℃; for 16 h; Step 2: 3-oxo-3,4-dihvdro-2H-benzorbiri .41oxazin-6-vlboronic acid; A mixture of 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2H-benzo[b][1 ,4]oxazin-3(4H)-one (500 mg, 1.82 mmol), polymer supported phenyl boronic acid (2200 mg, 6.4 mmol), 1 M aqueous hydrochloric acid (132 mg, 3.63 mmol) in acetonitrile (12 ml_) was stirred at room temperature 16 h. The reaction mixture was filtered and concentrated to yield the title compound as a solid (232 mg, 66percent). 1 H NMR (400 MHz, METHANOL-dΛ) δ ppm 4.79 (2 H, s), 6.94 (1 H, d, J=8.0 Hz), 7.18 (1 H, d, J=1.2 Hz), 7.27 (1 H, dd, J=8.0, 1.4 Hz).
Reference: [1] Patent: WO2010/116282, 2010, A1, . Location in patent: Page/Page column 56
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