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Product Details of [ 149524-42-5 ]

CAS No. :149524-42-5 MDL No. :MFCD08234640
Formula : C10H10FNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :XYUGDJIYKLSISX-SECBINFHSA-N
M.W : 211.19 Pubchem ID :11229590
Synonyms :

Calculated chemistry of [ 149524-42-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.88
TPSA : 49.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 0.94
Log Po/w (WLOGP) : 1.18
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 1.22
Consensus Log Po/w : 1.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.91
Solubility : 2.62 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 5.66 mg/ml ; 0.0268 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.08
Solubility : 1.76 mg/ml ; 0.00836 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.59

Safety of [ 149524-42-5 ]

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 [ 149524-42-5 ]

* 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 [ 149524-42-5 ]
  • Downstream synthetic route of [ 149524-42-5 ]

[ 149524-42-5 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 60456-26-0 ]
  • [ 149524-47-0 ]
  • [ 149524-42-5 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.33333 h; Inert atmosphere
Stage #2: at -78℃; for 1 h; Inert atmosphere
General procedure: Compound 2 (2 mmol) was dissolved in anhydrous THF (10 mL) then cooled to -78 C under nitrogen followed by slow addition of 1M LHMDS in THF solution (1.7 mL, 1.7 mmol) over 20 min. The resulting mixture was subsequently stirred at -78° C for 1 h before (R)-(-)-glycidyl butyrate (0.24 g, 1.7 mmol) was added drop wise at -78° C and the mixture was stirred at this temperature for 1 h then allowed to gradually warm to room temperature under stirring for 12 hrs. The reaction was quenched with DDW (10 mL) followed by EtOAc (4 mL). Then the two layers were separated and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (3×5 mL), dried over Na2SO4, filtered, and concentrated under vacuum.  The crude product was then dissolved in DCM (10 mL) and allowed to stand overnight to get a white precipitate which was filtered and washed with DCM.
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: at -78 - 20℃; Inert atmosphere
To a solution of N-carbobenzyloxy-3-fluoroaniline 2 (132 g, 538 mmol) in THF (1.3 L) at -78 °C added slowly n-butyllithium 1.6 M in n-hexane (370 mL, 600 mmol) under nitrogen condition. After the solution was stirred at -78 °C for 10 min, (R)-(-)-glycidyl butylate (84.0 mL, 600 mmol) was slowly added. The mixture was stirred at -78 °C for 2 h and stirred at room temperature for 24 h. After completion of the reaction, an aqueous saturated ammonium chloride (NH4Cl) solution was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was recrystallized from EtOAc and n-hexane to give the title compound (80 g, 70percent). 1H NMR (DMSO-d6): δ 7.51 (d, J = 12.0 Hz, 1H), 7.40 (m, 1H), 7.34 (m, 1H), 6.93 (t, J = 6.8 Hz, 1H), 5.21 (t, J = 5.6 Hz, 1H), 4.70 (m, 1H), 4.07 (t, J = 9.2 Hz, 1H), 3.83 (m, 1H), 3.68 (m, 1H), 3.55 (m, 1H).
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 26 h;
Will be 132 gramsN-Benzyloxycarbonyl-3-fluoroaniline was dissolved1.3 liters of tetrahydrofuran,And the solution was cooled to -78 ° C.370 ml of n-butyllithium (1.6 mol / l, n-hexane) was slowly added to the solution under a nitrogen atmosphere and then stirred for 10 minutes.Will be 84 ml(R) - (-) - butyric acid glycidyl ester was slowly added to the reaction mixture,Glycidyl butyrateThe mixture was stirred at the same temperature for 2 hours and then allowed to react at room temperature for 24 hours. After completion of the reaction, an ammonium chloride solution was added to the solution and extracted with 0.5 liter of ethyl acetate at room temperature. The resulting organic layer was separated by brine and dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was dissolved in 100 ml of ethyl acetate and washed with n-hexane to give a white crystal which was purified to 80 g of the title compound in 70percent yield.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5310 - 5321
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1027 - 1039
[3] Patent: CN106146559, 2016, A, . Location in patent: Paragraph 0044; 0045
[4] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 9, p. 1009 - 1014
[5] Patent: US2010/234615, 2010, A1, . Location in patent: Page/Page column 36
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5266 - 5269
[7] Patent: WO2016/77818, 2016, A1, . Location in patent: Paragraph 0210; 0212
[8] Patent: WO2017/200979, 2017, A1, . Location in patent: Paragraph 0195
  • 2
  • [ 60456-26-0 ]
  • [ 149524-42-5 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h;
Stage #2: at -78 - 20℃; for 26 h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane at 20℃;
132g of N-carbobenzyloxy-3-fluoroaniline 132g prepared in the Preparation example 1 was dissolved in 1.3L of tetrahydrofuran and the solution was cooled to- 78 °C. 370ml of n-buthyllitium (n-BuLi, 1. 6M/n-hexane) was slowly added to the solution in a nitrogen atmosphere, followed by stirring for 10 min. And 84ml of (R)- (-) -glycidylbuthylate was slowly added to the reaction mixture, stirred at the same temperature for 2 hours and allowed to react for 24 hours at room temperature. After completion of the reaction, the solution was added with ammonium chloride (NH4Cl) solution and extracted with 0. 5L of ethyl acetate at room temperature. The organic layer, thus separated, was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in 100ml of ethyl acetate and washed with n-hexane to give white crystals, which were purified to the title compound. 80g. Yield 70percent. IH NMR (DMSO-d6) 6 7. 85 (t, lH), 7.58 (dd, lH), 7.23 (dd, lH), 4.69 (m, lH), 4.02 (t, lH), 3.80 (dd, lH), 3.60 (br dd, 2H).
Reference: [1] Patent: WO2005/58886, 2005, A1, . Location in patent: Page/Page column 24
[2] Patent: WO2005/116017, 2005, A1, . Location in patent: Page/Page column 22-23
  • 3
  • [ 121906-41-0 ]
  • [ 149524-47-0 ]
  • [ 149524-42-5 ]
YieldReaction ConditionsOperation in experiment
91.6%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 26 h; Inert atmosphere
To a solution of N-carbobenzyloxy-3-fluoroaniline 3 (39.00 g, 159 mmol) in anhydrous THF (200 mL) at −78 °C was slowly added n-butyllithium 2.5 M in n-hexane (71.3 mL, 178 mmol) under argon condition. After the solution was stirred at −78 °C for 10 min, (R)-(−)-glycidyl butylate (24.9 mL, 178 mmol) was slowly added. The mixture was stirred at −78°C for 2 h and stirred at room temperature for 24 h. After completion of the reaction, an aqueous saturated ammonium chloride solution (150 mL) was added and the mixture was extracted with ethyl acetate (200 mL × 2). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was recrystallized from 20 percent ethyl acetate in petroleum ether to give the title compound (30.75 g, 91.6 percent). The 1H-NMR spectra were in accordance with the literature data.8) 1H-NMR (400 MHz, DMSO-d6) δ: 7.51–7.54 (m, 1H), 7.38–7.42 (m, 1H), 7.31–7.34 (m, 1H), 6.91–6.96 (m, 1H), 5.21 (t, 1H, J = 5.6 Hz), 4.68–4.73 (m, 1H), 4.08 (t, 1H, J = 9.2 Hz), 3.81–3.85 (m, 1H), 3.65–3.67 (m, 1H), 3.56–3.57 (m, 1H).
Reference: [1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 143 - 146
  • 4
  • [ 530-62-1 ]
  • [ 149524-42-5 ]
YieldReaction ConditionsOperation in experiment
87.8% With triethylamine In N,N-dimethyl-formamide at 65℃; for 4 h; In a 250 ml reaction flask,Compound (4) (12.8 g, 50 mmol) was added,N, N'-carbonyldiimidazole (CDI) (8.9 g, 55 mmol),DMF 100 ml,Triethylamine (15.1 g, 0.15 mol),Temperature control at 65 ,The reaction was carried out for 4 hours,After completion of the reaction,To room temperature,Extraction with dichloromethane / water (V / V = 1: 1)The aqueous layer was washed twice with dichloromethane,The organic layers were combined,Dried over anhydrous sodium sulfate,And concentrated to give the compound (5) (9.3 g) in a total yield of 87.8percent.
Reference: [1] Patent: CN105859780, 2016, A, . Location in patent: Paragraph 0035
  • 5
  • [ 72755-13-6 ]
  • [ 60456-26-0 ]
  • [ 149524-42-5 ]
YieldReaction ConditionsOperation in experiment
72.1 g
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -65 - -60℃; for 0.166667 h; Inert atmosphere
Stage #2: at -65 - 25℃; for 20 h; Inert atmosphere
Methyl (3-fluorophenyl)carbamate (Formula IV, 70 g, Example 1) was dissolved in anhydrous tetrahydrofuran (420 mL) at ambient temperature, and then the solution wascooled to -65°C to -60°C under nitrogen atmosphere. n-Butyl lithium (1.6 M in hexane, 272 mL) was slowly added to the solution under nitrogen atmosphere, and then the reaction mixture was stirred for 10 minutes. (R)-(-)-Glycidyl butyrate (Formula V, when R1= n-propyl, 60.25 g) was slowly added to the reaction mixture under nitrogenatmosphere at -65°C to -60°C, and then the mixture was stirred for 20 hours at 20°C to25°C under nitrogen atmosphere. After completion of the reaction, ammonium chloride solution (7 g in 70 mL of deionized water) was added to the reaction mixture. Tetrahydrofuran was recovered under vacuum at 40°C to 45°C, followed by the addition of deionized water (500 mL) at 40°C to 45°C. The reaction mixture was allowed to attainambient temperature and then was stirred for two hours. The solid obtained was filtered, and then washed with deionized water (70 mL). The wet solid was dried at 50°C to 55°C to afford the title compound.Yield: 72.1 g
Reference: [1] Patent: WO2016/88103, 2016, A1, . Location in patent: Page/Page column 14; 15
  • 6
  • [ 60456-26-0 ]
  • [ 149524-47-0 ]
  • [ 149524-42-5 ]
Reference: [1] Patent: US5565571, 1996, A,
  • 7
  • [ 372-19-0 ]
  • [ 149524-42-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1027 - 1039
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5266 - 5269
[3] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 143 - 146
[4] Patent: WO2016/77818, 2016, A1,
[5] Patent: WO2016/88103, 2016, A1,
[6] Patent: CN105859780, 2016, A,
[7] Patent: CN106146559, 2016, A,
[8] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5310 - 5321
[9] Patent: WO2017/200979, 2017, A1,
  • 8
  • [ 402-67-5 ]
  • [ 149524-42-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5266 - 5269
  • 9
  • [ 60456-26-0 ]
  • [ 404-71-7 ]
  • [ 149524-42-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 9, p. 1009 - 1014
  • 10
  • [ 149524-42-5 ]
  • [ 444335-16-4 ]
YieldReaction ConditionsOperation in experiment
92% With silver trifluoroacetate; bromine chloride In acetonitrile at 20℃; for 24 h; Will be 30 grams(R) -3- (3-fluorophenyl) -2-oxo-5-oxazolidinylmethanolDissolved in 300 ml of acetonitrile,And will be 46 gramsSilver trifluoroacetate(CF3COOAg) and 30.5 g of BrCl were added to the solution,After stirring at room temperature for 1 day, water was added to the solution and extracted with ethyl acetate. The resulting organic layer was separated and washed with brine and dehydrated. The residue was then filtered, concentrated in vacuo and dried, yielding 37.8 g of the title compound in 92percent yield.
Reference: [1] Patent: CN106146559, 2016, A, . Location in patent: Paragraph 0044; 0046
[2] Patent: WO2009/120789, 2009, A1, . Location in patent: Page/Page column 58
  • 11
  • [ 149524-42-5 ]
  • [ 856866-72-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 143 - 146
[2] Patent: CN105859780, 2016, A,
[3] Patent: WO2016/88103, 2016, A1,
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