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[ CAS No. 775304-57-9 ] {[proInfo.proName]}

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Chemical Structure| 775304-57-9
Chemical Structure| 775304-57-9
Structure of 775304-57-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 775304-57-9 ]

CAS No. :775304-57-9 MDL No. :
Formula : C15H9FN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :OOUGLTULBSNHNF-UHFFFAOYSA-N
M.W : 284.24 Pubchem ID :11219835
Synonyms :
PTC124

Calculated chemistry of [ 775304-57-9 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 72.09
TPSA : 76.22 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) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.45
Log Po/w (XLOGP3) : 3.09
Log Po/w (WLOGP) : 3.66
Log Po/w (MLOGP) : 3.08
Log Po/w (SILICOS-IT) : 3.19
Consensus Log Po/w : 3.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.95
Solubility : 0.0319 mg/ml ; 0.000112 mol/l
Class : Soluble
Log S (Ali) : -4.36
Solubility : 0.0125 mg/ml ; 0.0000438 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.55
Solubility : 0.000803 mg/ml ; 0.00000282 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 775304-57-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 775304-57-9 ]

* 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 [ 775304-57-9 ]
  • Downstream synthetic route of [ 775304-57-9 ]

[ 775304-57-9 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 692771-01-0 ]
  • [ 775304-57-9 ]
YieldReaction ConditionsOperation in experiment
85% With basic cobalt(II) carbonate; sodium bromide In acetic acid at 95℃; for 11 h; Green chemistry General procedure: Oxidation process was carried out in an ideal mixing reactor. A starting methylarene 1a—h (13 mmol), cobalt acetate (1.3 mmol), and sodium bromide (1.3 mmol) were dissolved in glacial acetic acid (40 mL). Then, the solution was heated to 95 °C and air was fed to the reactor. The reaction mixture was allowed to stand for 11 h at 95 °C and cooled to ~20 °C, a precipitate formed was filtered.#10;
Reference: [1] Russian Chemical Bulletin, 2015, vol. 64, # 1, p. 142 - 145[2] Izv. Akad. Nauk, Ser. Khim., 2015, # 1, p. 142 - 145,4
[3] New Journal of Chemistry, 2014, vol. 38, # 7, p. 3062 - 3070
  • 2
  • [ 775304-60-4 ]
  • [ 775304-57-9 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: at 100℃; for 2 h; Heating / reflux
Stage #2: With hydrogenchloride In water
To a solution of 3-[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-3-yl]-benzoic acid methyl ester (3.3 g, 111 mmol) in THF (40 mL) was added 1.5M aqueous NaOH (10 mL, 14 mmol). The reaction mixture was refluxed for 2 h at 100° C. The organic solvent was removed and the aqueous solution was diluted with water (50 mL), and then acidified with aqueous HCl. The white precipitate was filtered off and the white cake was washed with cold water and then dried using lyophilizer. The desired acid (3.0 g, 96percent yield) was obtained as a white powder with 98percent purity (LC/UV). Melting point 242° C.; IR υ 3000 (Aromatic C-H), 1710 (CO); 1H-NMR (D6-DMSO) δ 8.31 (1H), 8.18 (2H), 8.08 (1H), 7.88 (2H), 7.51 (2H); 13C-NMR (D6-DMSO) δ 172.71, 167.38, 166.48, 161.25, 135.80, 132.24, 131.79, 131.79, 131.08, 130.91, 129.81, 127.76, 125.48, 117.38, 111.70; 19F-NMR (D6-DMSO) δ 109.7.
96%
Stage #1: With sodium hydroxide; water In tetrahydrofuran at 100℃; for 2 h; Heating / reflux
Stage #2: With hydrogenchloride In water
To a solution of 3-[5-(2-Fluoro-phenyl)-[l,2,4]oxadiazol-3-yl]-benzoic acid methyl ester (3.3g, 11 mmol) in THF (40 mL) was added 1.5M aqueous NaOH (10 mL, 14 mmol). The reaction mixture was refluxed for 2h at 100 °C. The organic solvent was removed and the aqueous solution was diluted with water (50 mL), and then acidified with aqueous HCl. The white precipitate was filtered off and the white cake was washed with cold water and then dried using lyophilizer. The desired acid (3.Og5 96percent yield) was obtained as a white powder with 98percent purity (LC/UV). Melting point 242 °C; IR D 3000 (Aromatic C-H), 1710 (C=O); 1H-NMR (D6-DMSO) δ 8.31 (IH), 8.18 (2H)3 8.08 (IH), 7.88 (2H), 7.51 (2H); 13C- NMR (D6-DMSO) δ 172.71, 167.38, 166.48, 161.25, 135.80, 132.24, 131.79, 131.79, 131.08, 130.91, 129.81, 127.76, 125.48, 117.38, 111.70; 19F-NMR (D6-DMSO) δ 109.7.
96%
Stage #1: With sodium hydroxide; water In tetrahydrofuran at 100℃; for 2 h; Heating / reflux
Stage #2: With hydrogenchloride In water
To a solution of 3-[5-(2-Fluoro-phenyl)-[l ,2,4]oxadiazol-3-yl]-benzoic acid methyl ester (3.3g, 1 1 mmol) in THF (40 mL) was added 1.5M aqueous NaOH (10 mL, 14 mmol). The reaction mixture was refluxed for 2h at 100 0C. The organic solvent was removed and the aqueous solution was diluted with water (50 mL), and then acidified with aqueous HCl. The white precipitate was filtered off and the white cake was washed with cold water and then dried using lyophilizer. The desired acid (3.0g, 96percent yield) was obtained as a white powder with 98percent purity (LC/UV). Melting point 242 0C; IR 3000 (Aromatic C-H),ATI-2289908vl 25 <n="27"/>1710 (C=O); 1H-NMR (D6-DMSO) δ 8.31 (IH), 8.18 (2H), 8.08 (IH), 7.88 (2H), 7.51 (2H); 13C-NMR (D6-DMSO) δ 172.71, 167.38, 166.48, 161.25, 135.80, 132.24, 131.79, 131.79, 131.08, 130.91, 129.81, 127.76, 125.48, 1 17.38, 1 11.70; 19F-NMR (D6-DMSO) δ 109.7.
96%
Stage #1: With sodium hydroxide; water In tetrahydrofuran at 100℃; for 2 h;
Stage #2: With hydrogenchloride In water
To a solution of 3-[5-(2-Fluoro-phenyl)-[l ,2,4]oxadiazol-3-yl]-benzoic acid methyl ester (3.3g, 11 mmol) in THF (40 niL) was added 1.5M aqueous NaOH (10 niL, 14 mmol). The reaction mixture was refluxed for 2h at 100 0C. The organic solvent was removed and the aqueous solution was diluted with water (50 mL), and then acidified with aqueous HCl. The white precipitate was filtered off and the white cake was washed with cold water and then dried using lyophilizer. The desired acid (3.Og, 96percent yield) was obtained as a white powder with 98percent purity (LC/UV). Melting point 242 0C; IR D 3000 (Aromatic C-H), 1710 (C=O); 1H-NMR (D6-DMSO) δ 8.31 (IH), 8.18 (2H), 8.08 (IH), 7.88 (2H), 7.51 (2H); 13C-NMR (D6-DMSO) δ 172.71, 167.38, 166.48, 161.25, 135.80, 132.24, 131.79, 131.79, 131.08, 130.91, 129.81, 127.76, 125.48, 117.38, 111.70; 19F-NMR (D6-DMSO) δ 109.7.
123 mg With water; sodium hydroxide In ethanol at 20℃; for 3 h; General procedure: To a solution of methyl ester 13 (228 mg, 0.76 mmol) in EtOH: H2O (3:2, 10 mL) was added crushed NaOH (91 mg, 2.27 mmol) and the solution was stirred at rt for 3h. The volatiles were evaporated under reduced pressure and the residue obtained was acidified with 1N aqueous HCl (pH ~ 4). This solution was then transferred to a separatory funnel and extracted with EtOAc (3 x 20 mL). The combined organic layers were dried Na2SO4 and concentrated under reduced pressure to afford the title acid 14 (123 mg, 54percent) as a white solid.
3 g With water; sodium hydroxide In tetrahydrofuran at 100℃; for 2 h; A solution of 33 g of methyl 3- [5- (2-fluorophenyl) - [1,2,4-oxadiazol-3-yl] -benzoic acid methyl ester was dissolved in 400 mlOf tetrahydrofuran,To this was added 100 ml of a 1.5 M aqueous solution of sodium hydroxide.The reaction mixture was heated at 100 ° C for 2 hours. The solvent was removed under reduced pressure,The aqueous solution was stirred at 5 ° C for 2 hours.The organic solvent was removed, the aqueous solution was diluted with 50 ml of water,Followed by acidification with hydrochloric acid to pH 1. Filter out a white precipitate, wash the filter cake with cold water,And then dried with a freeze drier.To obtain 3. 0 g of 3- [5- (2_ fluorophenyl) - [1,2,4] oxadiazol-3-yl] benzoic acid. (1H), 8.18 (2H), 08.8 (1H), 7.88 (2H), 7.11 (2H). Show that the sample prepared in Preparation Example 1 was incubated with TO2004091502A2 Example 2 prepared ataluren

Reference: [1] Patent: US2004/204461, 2004, A1, . Location in patent: Page 54
[2] Patent: WO2007/117438, 2007, A2, . Location in patent: Page/Page column 261
[3] Patent: WO2008/45566, 2008, A1, . Location in patent: Page/Page column 25-26
[4] Patent: WO2006/110483, 2006, A1, . Location in patent: Page/Page column 21
[5] Advanced Synthesis and Catalysis, 2017, vol. 359, # 5, p. 772 - 778
[6] Patent: WO2008/30570, 2008, A1, . Location in patent: Page/Page column 20-21
[7] Patent: WO2008/30570, 2008, A1, . Location in patent: Page/Page column 21-23
[8] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2473 - 2476
[9] Patent: CN105461650, 2016, A, . Location in patent: Paragraph 0075; 0082
  • 3
  • [ 199447-10-4 ]
  • [ 445-29-4 ]
  • [ 775304-57-9 ]
YieldReaction ConditionsOperation in experiment
65% With tetrachloromethane; diethoxymethylsilane; Bis(p-nitrophenyl) phosphate; triphenylphosphine In toluene at 120℃; for 24 h; Reflux; Large scale To the reactor was added o-fluorobenzoic acid (4,140 g, 1 mol), compound 3 (180 g, 1 mol), triphenylphosphine(52.4 g, 0.2 mol) carbon tetrachloride (152 g, 1 mol), diethoxymethylsilane (202.6 g, 1.2 mol)Bis (p-nitrophenyl) phosphate (17.1 g, 0.05 mol),500mL of toluene. 120 oil bath heated to reflux condensation reaction for 24 hours. Until the reaction liquid coldAfter that, it was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was purified by column chromatography to give the title compoundAtaluren (1,184.6 g) as a white solid in 65percent yield
Reference: [1] Patent: CN106279057, 2017, A, . Location in patent: Paragraph 0023; 0024
  • 4
  • [ 393-52-2 ]
  • [ 775304-57-9 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With hydroxylamine In water; <i>tert</i>-butyl alcohol at 38 - 41℃; for 21 h;
Stage #2: With triethylamine In water; <i>tert</i>-butyl alcohol at 27 - 40℃; for 7 h;
3-[5-(2-fluorophenylHl,2,41oxad-azol-3-vπ-benzoic acid: One pot process; Reflux <n="25"/>[0188] A reactor vessel was charged with 3-Cyanobenzoic acid (7.35 g) and molten ter/-butanol (100 raL). The vessel was sealed and the batch temperature was set to 600C and the agitator was started. The suspension was stirred for Ih and then the batch temperature was set to 400C. 50percent aqueous hydroxylamine (3.63 g) was charged to the reactor in an inert atmosphere over 3 hours. The batch temperature was maintained at 38- 410C during the addition. The reaction was completed after stirring for 18 hours at 400C. [0189] The batch was cooled to 27°C and charged with triethylamine (5.56 g) over 2 minutes. 2-Fluorobenzoyl chloride (7.82 g) was added over 3 hours. The batch temperature was maintained at 24-27°C during the addition. The batch was stirred for further 4 hours at 400C.[0190] The batch was heated to 790C over 30 minutes and stirred for 16 hours at about 79°C. To the white suspension was added water (100 mL) over 3 hours while the batch temperature was maintained at 700C. The batch was charged with 37percent aqueous hydrochloric acid over 20 minutes. The pH of the batch was determined to be about 2.2, by a pH meter and stirring at about 700C was continued for about an additional 1 hour. [0191] The batch was cooled in a linear fashion from 700C to 300C over 3 hours and the slurry was transferred into a filter. Filtration was complete after 5 minutes. The filter cakes were washed with fer/-butanol (50 mL, 40 0C) over 5 minutes. Purified water (100 mL, 600C) was applied to the cakes as the final wash. The cakes were dried in a vacuum oven at 70 0C for 18 hour and then discharged. Purity was determined to be about 98.68percent. The overall yield of isolated product was about 76percent (10.8 g).
Reference: [1] Patent: WO2008/30570, 2008, A1, . Location in patent: Page/Page column 23-24
  • 5
  • [ 13531-48-1 ]
  • [ 775304-57-9 ]
Reference: [1] Patent: CN105461650, 2016, A,
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 5, p. 772 - 778
[3] Patent: WO2006/110483, 2006, A1,
  • 6
  • [ 1877-72-1 ]
  • [ 775304-57-9 ]
Reference: [1] Patent: CN105461650, 2016, A,
[2] Patent: US2017/362192, 2017, A1,
  • 7
  • [ 1141475-82-2 ]
  • [ 775304-57-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 5, p. 772 - 778
[2] Patent: WO2006/110483, 2006, A1,
  • 8
  • [ 445-29-4 ]
  • [ 775304-57-9 ]
Reference: [1] New Journal of Chemistry, 2014, vol. 38, # 7, p. 3062 - 3070
  • 9
  • [ 20680-59-5 ]
  • [ 775304-57-9 ]
Reference: [1] New Journal of Chemistry, 2014, vol. 38, # 7, p. 3062 - 3070
  • 10
  • [ 15676-11-6 ]
  • [ 775304-57-9 ]
Reference: [1] Patent: CN105461650, 2016, A,
  • 11
  • [ 24964-64-5 ]
  • [ 775304-57-9 ]
Reference: [1] Patent: US2017/362192, 2017, A1,
  • 12
  • [ 775304-80-8 ]
  • [ 775304-57-9 ]
Reference: [1] Patent: WO2006/110483, 2006, A1,
  • 13
  • [ 1141475-82-2 ]
  • [ 393-52-2 ]
  • [ 775304-57-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2473 - 2476
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