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[ CAS No. 524684-52-4 ] {[proInfo.proName]}

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Chemical Structure| 524684-52-4
Chemical Structure| 524684-52-4
Structure of 524684-52-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 524684-52-4 ]

CAS No. :524684-52-4 MDL No. :MFCD09954141
Formula : C15H10FNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MQIMZDXIAHJKQP-UHFFFAOYSA-N
M.W : 271.24 Pubchem ID :656954
Synonyms :
ERB-041

Calculated chemistry of [ 524684-52-4 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 73.54
TPSA : 66.49 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.5
Log Po/w (XLOGP3) : 3.59
Log Po/w (WLOGP) : 4.0
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 3.66
Consensus Log Po/w : 3.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.21
Solubility : 0.0169 mg/ml ; 0.0000622 mol/l
Class : Moderately soluble
Log S (Ali) : -4.67
Solubility : 0.00576 mg/ml ; 0.0000212 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.01
Solubility : 0.00267 mg/ml ; 0.00000984 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.97

Safety of [ 524684-52-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 524684-52-4 ]

* 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 [ 524684-52-4 ]
  • Downstream synthetic route of [ 524684-52-4 ]

[ 524684-52-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 74-85-1 ]
  • [ 544704-73-6 ]
  • [ 524684-52-4 ]
YieldReaction ConditionsOperation in experiment
71.5% With triethylamine In acetonitrile at 75℃; for 16 h; Example 1; Preparation of 2-(3-Fluoro-4-hydroxyphenyl)-7-vinylbenzooxazol-5-ol A 2 gallon hydrogenator was charged with 2-(3-Fluoro-4-hydroxyphenyl)-7-bromobenzooxazol-5-ol (300 g, 0.926 mole), tri-o-tolylphosphine (9.1 g, 3.3percent), palladium diacetate (2.1 g 1percent), acetonitrile (4.5 L), and triethylamine (375 g, 4 eq). The hydrogenator was flushed with nitrogen, and with ethylene; and then the pressure was adjusted to 50 psi. The reaction mixture was heated to 75° C. and held for 16 hours, at which time HPLC sampling indicated 0.2percent of starting material remaining. The mixture was cooled to 35-40° C. and filtered through a 0.2μ cartridge, and washed with 1,2-diethoxyethane (1.2 L). The filtrate was concentrated under vacuum to 1.2 L, and water (1.5 L) and 1,2-diethoxyethane (1.2 L) were added. The pH was adjusted to 11-12 by adding 1.4 L of 2N NaOH at 15-20° C. The phases were separated, and the organic phase was extracted with water (300 ml), and 2 N NaOH (20 mL). The combined aqueous phase was washed with 1,2-diethoxyethane (2.x.900 mL). The pH was adjusted to 2.5-3.5 by adding 500 mL of 4N HCl at 15-20° C. After holding for 4 hours, the solid was filtered off and washed with water (3.x.200 mL). The wet cake was suspended in acetone (1822 mL) and heated to 54-60° C. then held for complete solution. While maintaining at 54-60° C. acetonitrile was added (1822 mL) over 0.5 hour. The solution was concentrated by distilling at atmospheric pressure to a volume of 1.8-2.0 L, then the concentrate was cooled to 45-50° C. and held for 0.5 hour; then cooled to -3 to 3° C. and held for 1 hour. The solid was filtered off and washed with precooled acetonitrile (2.x.200 mL); then dried in a vacuum oven at 55-65° C. and 5-10 mm Hg for 24 hours to give 180 g (71.5percent yield) of product. The product from above was dissolved in ethyl acetate (23 volumes) at 75-80° C. The resulting solution was cooled back to 25-45° C. and treated with charcoal. The filtrate was then concentrated at atmospheric pressure to 7 volumes, and to the slurry was added heptane (6 volumes) while maintaining at 75-80° C. The solution was then cooled to 45-50° C., held for 0.5 hour, then cooled to 0-5° C., and held for 1 hour. The solid was filtered off, dried at 55-65° C., 5-10 mmHg, to afford an 87percent recovery and 99.4percent purity.
58% With triethylamine In acetonitrile at 75℃; for 16 h; EXAMPLE 1; Preparation of 2-(3-Fluoro-4-hydroxyphenyl)-7-vinylbenzoxazol-5-ol A 2 gallon hydrogenator was charged with 2-(3-Fluoro-4-hydroxyphenyl)-7-bromobenzoxazol-5-ol (300 g, 0.926 mole), tri-o-tolylphosphine (9.1 g, 3.3percent), palladium diacetate (2.1 g 1percent), acetonitrile (4.5 L), and triethylamine (375 g, 4 eq). The hydrogenator was flushed with nitrogen, and with ethylene; and then the pressure was adjusted to 50 psi. The reaction mixture was heated to 75° C. and held for 16 hours, at which time HPLC sampling indicated 0.2percent of starting material remaining. The mixture was cooled to 35-40° C. and filtered through a 0.2μ cartridge, and washed with 1,2-diethoxyethane (1.2 L). The filtrate was concentrated under vacuum to 1.2 L, and water (1.5 L) and 1,2-diethoxyethane (1.2 L) were added. The pH was adjusted to 11-12 by adding 1.4 L of 2N NaOH at 15-20° C. The phases were separated, and the organic phase was extracted with water (300 ml), and 2 N NaOH (20 mL). The combined aqueous phase was washed with 1,2-diethoxyethane (2.x.900 mL). The pH was adjusted to 2.5-3.5 by adding 500 mL of 4N HCl at 15-20° C. After holding for 4 hours, the solid was filtered off and washed with water (3.x.200 mL). The product was then recrystallized twice from an ethanol:water solution as described below. The wet cake was suspended in ethanol (1055 mL) and heated to 74-80° C. While maintaining at 74-80° C., water (422 mL) was added. The solution was cooled to 45-55° C. and held for 0.5 hour, then cooled to 0-8° C. and held for 1 hour. The solid was filtered off and washed with a precooled solution of ethanol:water (2:1) (2.x.200 mL). The wet cake was then suspended in ethanol (945 mL) and heated to 74-80° C. While maintaining at 74-80° C., water (472 mL) was added. The solution was cooled to 45-55° C. and held for 0.5 hour, then cooled to 0-8° C. and held for 1 hour. The solid was filtered off and washed with a precooled solution of ethanol:water (2:1) (2.x.200 mL). The product was dried in a vacuum oven at 55-65° C. and 5-10 mm Hg for 24 hours to afford 146 g of 2-(3-Fluoro-4-hydroxyphenyl)-7-vinylbenzoxazol-5-ol (58percent yield).
Reference: [1] Patent: US2006/199967, 2006, A1, . Location in patent: Page/Page column 5-6
[2] Patent: US2006/199852, 2006, A1, . Location in patent: Page/Page column 6
  • 2
  • [ 7486-35-3 ]
  • [ 544704-73-6 ]
  • [ 524684-52-4 ]
YieldReaction ConditionsOperation in experiment
72% at 115℃; for 48 h; Dichlorobis(tri-otolylphosphine)palladium (II) (0.87 g, 1.1 mmol) was added into a mixture of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (7.16 g, 22.1 mmol), tributyl(vinyl)tin (10.5 g, 33.25 mmol) and ethylene glycol diethyl ether (65 mL). The reaction mixture was stirred at 115° C. for 48 hours, cooled to room temperature and treated with activated carbon. The reaction mixture was filtered through MgSO4 and concentrated. Purification by flash chromatography, on acidic silica gel (hexanes/EtOAc/CH2Cl2 1/1/1), gave a white solid (4.35 g, 72percent yield, m.p. 250-252° C.); MS m/e 272 (M+H)+. Analysis for: C15H10FNO3 Calc'd: C, 66.42; H, 3.72; N, 5.16 Found: C, 66.03; H, 3.68; N, 5.09
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
[2] Patent: US2006/46968, 2006, A1, . Location in patent: Page/Page column 29-30
  • 3
  • [ 544704-81-6 ]
  • [ 524684-52-4 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogen fluoride In tetrahydrofuran; water; acetonitrile at 65℃; for 8 h; Hydrofluoric acid (48 wt. percent in water, 1 mL) was added into a solution of 5-[tert-butyl(dimethyl)silyl]oxy}-2-(4-[tert-butyl(dimethyl)silyl]oxy}-3-fluorophenyl)-7-vinyl-1,3-benzoxazole (1.5 g, 3.0 mmol), THF (6 mL) and acetonitrile (3 mL). The reaction mixture was stirred at 65° C. for 8 hours, and then poured into water. The precipitated solid was filtered off and dried. Crystallization of the product from acetone/ethyl ether gave a white solid (0.72 g, 81percent yield, m.p. 249-251° C.); MS m/e 272 (M+H)+. Analysis for: C15H10FNO3 Calc'd: C, 66.42; H, 3.72; N, 5.16 Found: C, 66.31; H, 3.85; N, 4.96
Reference: [1] Patent: US2006/46968, 2006, A1, . Location in patent: Page/Page column 29
  • 4
  • [ 544704-84-9 ]
  • [ 524684-52-4 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: With potassium carbonate In 1,4-dioxane at 90℃; for 1 h;
Stage #2: With hydrogenchloride In 1,4-dioxane; water
Potassium carbonate (55 mg) was added into a solution of 2-[4-(acetyloxy)-3-fluorophenyl]-7-vinyl-1,3-benzoxazol-5-yl acetate (0.14 g, 0.39 mmol) and 1,4-dioxane (3 mL). The reaction mixture was stirred at 90° C. for 1 hour, poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from EtOAc/hexanes, gave a white solid (0.06 g, 46percent yield, m.p. 250-252° C.); MS m/e 272 (M+H)+. Analysis for: C15H10FNO3 Calc'd: C, 66.42; H, 3.72; N, 5.16 Found: C, 66.32; H, 3.47; N, 5.18
Reference: [1] Patent: US2006/46968, 2006, A1, . Location in patent: Page/Page column 30
  • 5
  • [ 629-14-1 ]
  • [ 7486-35-3 ]
  • [ 544704-73-6 ]
  • [ 524684-52-4 ]
Reference: [1] Patent: US2003/199562, 2003, A1,
  • 6
  • [ 123-91-1 ]
  • [ 544704-84-9 ]
  • [ 524684-52-4 ]
Reference: [1] Patent: US2003/199562, 2003, A1,
  • 7
  • [ 1568-70-3 ]
  • [ 524684-52-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
  • 8
  • [ 403-20-3 ]
  • [ 524684-52-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
  • 9
  • [ 3907-15-1 ]
  • [ 524684-52-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
  • 10
  • [ 115929-59-4 ]
  • [ 524684-52-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
  • 11
  • [ 206872-01-7 ]
  • [ 524684-52-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
  • 12
  • [ 544704-75-8 ]
  • [ 524684-52-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
  • 13
  • [ 544704-74-7 ]
  • [ 524684-52-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5021 - 5040
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