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[ CAS No. 206055-91-6 ] {[proInfo.proName]}

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Chemical Structure| 206055-91-6
Chemical Structure| 206055-91-6
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Product Details of [ 206055-91-6 ]

CAS No. :206055-91-6 MDL No. :MFCD06656791
Formula : C10H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CBTFIJPSRUYXHW-UHFFFAOYSA-N
M.W : 254.08 Pubchem ID :11032412
Synonyms :

Calculated chemistry of [ 206055-91-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.77
TPSA : 46.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.04
Solubility : 0.23 mg/ml ; 0.000906 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.875 mg/ml ; 0.00344 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.44
Solubility : 0.00918 mg/ml ; 0.0000361 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.62

Safety of [ 206055-91-6 ]

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 [ 206055-91-6 ]

* 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 [ 206055-91-6 ]
  • Downstream synthetic route of [ 206055-91-6 ]

[ 206055-91-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 107-19-7 ]
  • [ 29203-58-5 ]
  • [ 206055-91-6 ]
YieldReaction ConditionsOperation in experiment
69% With triethylamine In dichloromethane at 20℃; for 1.5 h; -bromo-N-hydroxybenzimidoyl chloride (3.5 g, 14.9 mmol) synthesized in Step 2 of Preparation Example 6, propargyl alcohol (2.74 mL, 45 mmol) and triethylamine (Et3N, 7.7 mL) were added to methylene chloride (50 mL) and the reactants were stirred at room temperature for 1.5 hours. After completion of the reaction was confirmed by TLC, extraction was done with water (200 mL) and methylene chloride (500 mL). The organic layer was washed with water (100 mL.x.2) and brine (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate and hexane as a developing solvent, thus affording the title compound (3-(4-bromophenyl)isoxazol-5-yl)methanol (11e). Yield: 69percent.1H NMR (CDCl3, 400 MHz): 7.66 (d, 2H, J=2.4 Hz), 7.64 (d, 2H, J=1.6 Hz), 6.53 (s, 1H), and 4.81 (s, 2H).
69% With triethylamine In dichloromethane at 20℃; for 5 h; Step 1: Preparation of (3-(4-bromophenyI)isoxazol-5-vI)methanoI (lie)4-bromo-N-hydroxybenzimidoyl chloride (3.5 g, 14.9 mmol) synthesized in Step 2 ofPreparation Example 6, propargyl alcohol (2.74 mL, 45 mmol) and triethylamine (Et3N, 7.7 rnL) were added to methylene chloride (50 rnL) and the reactants were stirred at room temperature for 1.5 hours. After completion of the reaction was confirmed by TLC, extraction was done with water (200 mL) and methylene chloride (500 mL). The organic layer was washed with water (100 mL X 2) and brine (50 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate and hexane as a developing solvent, thus affording the title compound (3-(4-bromophenyl)isoxazol-5- yl)methanol (1 Ie). Yield: 69percent.1H NMR(CDCl3, 400MHz): 7.66(d, 2H, J=2.4Hz), 7.64(d, 2H, J=I.6Hz), 6.53(s, IH)5 and 4.81(s, 2H).
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 2, p. 284 - 302
[2] Patent: US2010/63041, 2010, A1, . Location in patent: Page/Page column 32
[3] Patent: WO2008/108602, 2008, A1, . Location in patent: Page/Page column 51; 31-32
  • 2
  • [ 107-19-7 ]
  • [ 206055-91-6 ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine In dichloromethane at 0 - 20℃; for 12 h; To a stirred solution of Z (500 mg, 2.132 mmol) in CH2CI2 (10 ml) was added propargyl alcohol (120 mg, 2.132 mmol) and followed by Et3N (0.34 ml 2.345 mmol) at 0 °C under inert atmosphere. The resulting reaction mixture was stirred for 12 h at RT. Progress of the reaction was monitored by TLC. The reaction mixture was then diluted with water and extracted with CH2CI2 (3x30 mL). The combined organic layer was washed with water, dried over anhydrous Na2S04 and concentrated under reduced pressure to obtain the crude. The crude material was purified by silica gel column chromatography eluting with 15-20percent EtOAc/hexane as eluent to afford AA (400 mg, 1.57 mmol, 73percent) as a white solid. *H NMR (500 MHz, CDC13): 5 7.67 (d, / = 8.5 Hz, 2H), 7.59 (d, / = 8.5 Hz, 2H), 6.54 (s , 1H), 4.83 (d, / = 4.5 Hz, 2H), 2.13 (bs, 1H). LC-MS: m/z 252 [M-2] " at 3.28 min (95.08percent purity).
Reference: [1] Patent: WO2014/117090, 2014, A1, . Location in patent: Page/Page column 100-101
  • 3
  • [ 25062-46-8 ]
  • [ 107-19-7 ]
  • [ 206055-91-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 3, p. 765 - 781
[2] Chemical Papers, 2015, vol. 69, # 11, p. 1500 - 1511
[3] Ultrasonics Sonochemistry, 2017, vol. 36, p. 343 - 353
[4] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 929 - 936
  • 4
  • [ 1122-91-4 ]
  • [ 206055-91-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 2, p. 284 - 302
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 3, p. 765 - 781
[3] Patent: WO2014/117090, 2014, A1,
[4] Chemical Papers, 2015, vol. 69, # 11, p. 1500 - 1511
[5] Ultrasonics Sonochemistry, 2017, vol. 36, p. 343 - 353
[6] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 929 - 936
[7] Patent: WO2008/108602, 2008, A1,
  • 5
  • [ 25062-46-8 ]
  • [ 206055-91-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 2, p. 284 - 302
[2] Patent: WO2014/117090, 2014, A1,
[3] Patent: WO2008/108602, 2008, A1,
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