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[ CAS No. 510729-01-8 ] {[proInfo.proName]}

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Chemical Structure| 510729-01-8
Chemical Structure| 510729-01-8
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Product Details of [ 510729-01-8 ]

CAS No. :510729-01-8 MDL No. :MFCD23381075
Formula : C14H11BrFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UPTMRBYILBFUPA-UHFFFAOYSA-N
M.W : 324.15 Pubchem ID :67274244
Synonyms :

Calculated chemistry of [ 510729-01-8 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 74.37
TPSA : 38.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.92
Log Po/w (XLOGP3) : 3.41
Log Po/w (WLOGP) : 4.41
Log Po/w (MLOGP) : 3.98
Log Po/w (SILICOS-IT) : 3.57
Consensus Log Po/w : 3.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.14
Solubility : 0.0237 mg/ml ; 0.0000732 mol/l
Class : Moderately soluble
Log S (Ali) : -3.89
Solubility : 0.0413 mg/ml ; 0.000127 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.17
Solubility : 0.00022 mg/ml ; 0.000000679 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.34

Safety of [ 510729-01-8 ]

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 [ 510729-01-8 ]

* 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 [ 510729-01-8 ]
  • Downstream synthetic route of [ 510729-01-8 ]

[ 510729-01-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 510729-01-8 ]
  • [ 60456-26-0 ]
  • [ 444335-16-4 ]
YieldReaction ConditionsOperation in experiment
87% With lithium tert-butoxide In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 0 - 20℃; for 3 h; 119 g (367 mmol) of Compound XXIX was dissolved in 300 mL of tetrahydrofuran/150 mL of dimethylformamide, 38.19 g (477 mmol) of lithium-t butoxide was slowly added dropwise thereto at 0°C, the resulting solution was stirred for 10 minutes, 63 mL (440 mmol) of (R)-glycidyl butyrate and 21 mL (550 mmol) of methanol were added thereto, and the resultant solution was stirred at room temperature for 3 hours. Subsequently, pH of the reaction mixture was adjusted to approximately 6 using an aqueous ammonium chloride solution and then the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in 1000 mL of 80percent ethylacetate/hexane, was sequentially washed with water and an aqueous saturated sodium chloride solution (brine), and then dehydrated using anhydrous sodium sulfate, followed by concentration under reduced pressure and column chromatography, to obtain 93 g (320 mmol) of Compound B-I as a white solid (yield: 87percent). [0162] 1H NMR (600 MHz, CDCl3) δ 7.53 (m, 2H), 7.15 (dd, J1 = 9.0 Hz, J2 = 2.4 Hz, 1H), 4.77 (m, 1H), 4.00 (m, 3H), 3.77 (m, 1H), 2.10 (t, J = 6.0 Hz, 1H)
87%
Stage #1: With lithium tert-butoxide In tetrahydrofuran; N,N-dimethyl-formamide at 0℃;
Stage #2: at 20℃; for 3 h;
Preparation of Compound B-I 119 g (367 mmol) of Compound XXIX was dissolved in 300 mL of tetrahydrofuran/150 mL of dimethylformamide, 38.19 g (477 mmol) of lithium-t butoxide was slowly added dropwise thereto at 0° C., the resulting solution was stirred for 10 minutes, 63 mL (440 mmol) of (R)-glycidyl butyrate and 21 mL (550 mmol) of methanol were added thereto, and the resultant solution was stirred at room temperature for 3 hours. Subsequently, pH of the reaction mixture was adjusted to approximately 6 using an aqueous ammonium chloride solution and then the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in 1000 mL of 80percent ethylacetate/hexane, was sequentially washed with water and an aqueous saturated sodium chloride solution (brine), and then dehydrated using anhydrous sodium sulfate, followed by concentration under reduced pressure and column chromatography, to obtain 93 g (320 mmol) of Compound B-I as a white solid (yield: 87percent). [0174] 1H NMR (600 MHz, CDCl3) δ 7.53 (m, 2H), 7.15 (dd, J1=9.0 Hz, J2=2.4 Hz, 1H), 4.77 (m, 1H), 4.00 (m, 3H), 3.77 (m, 1H), 2.10 (t, J=6.0 Hz, 1H)
86.4%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane; <i>tert</i>-butyl alcohol at 0℃; for 0.5 h;
Stage #2: at 0 - 20℃;
Butyl lithium (2.3M in n-hexanes, 118.3 ml, 0.272 mol, 1.06 eq) was added at -30° C. to anhydrous tert-butanol (25.0 g, 0.53 mol, 2.07 eq) in anhydrous THF (170 ml), under nitrogen.
The mixture was stirred for 30 min at -30° C., and was then allowed to warm slowly to 0° C. After 30 min at 0° C., the (4-bromo-3-fluoro-phenyl)-carbamic acid benzyl ester (83 g, 0.256 mol, 1 eq) was added portionwise, keeping the temperature cold, and the mixture was stirred for an additional 30 min at 0° C.
To this ice cold mixture, R(-)-glycidyl butyrate (39.7 ml, 0.288 mol, 1.12 eq) were added and the mixture allowed to come gradually to room temperature.
The mixture was extracted with saturated sodium chloride solution and the organic phase was dried over MgSO4, filtrated and evaporated.
The product was obtained after recrystallisation of the crude product with ethyl acetate, to give (64.1 g, 86.4percent).
80%
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.
65%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: at 20℃; for 24 h;
3.4.la (2.5 g, 7.7 mmol, 1.0 equiv) was dissolved in THE (20 mL) and cooled to -78°C. n-BuLi (2.5M in hexane) (0.59 g, 9.3 mmol, 1.2 equiv) was gradually added and the reaction mixture was stirred at -78 °C for 1 hour. (R)-oxiran-2-ylmethyl butyrate (1 .33 g, 9.3 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (80-100 percent EtOAc in Hexane) to afford product 3.4.lb which was carry forwarded for next step. (1.46 g, 65percent yield). LCMS (mlz): 292.1 [M+H].
45.3%
Stage #1: With ammonium chloride; lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.25 h;
Stage #2: at 20℃; for 61 h;
(4)
Preparation of (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin -2-one
Benzyl 4-bromo-3-fluorophenylcarbamate (20 g, 61.7 mmol) was dissolved in 180 mL THF, cooled to -78°C, and LiHMDS (1.0M in THF, 62.4 mL, 62.4 mmol) was added dropwise within 45 min.
After continued to stir for 30 min, R-glycidyl butyrate (2.21 mL, 62.3 mmol) was added dropwise.
After continued to react for 1 h at low temperature, it was warmed to room temperature and reacted for 60 h.
The reaction was quenched with saturated ammonium chloride.
Water was added, and extracted with ethyl acetate.
The organic phase was dried, concentrated, and then separated by a silica gel column (petroleum ether : ethyl acetate =2: 1) to obtain 8.1 g of (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one, at a yield of 45.3 percent.
45.3%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.25 h;
Stage #2: at -78 - 20℃; for 61 h;
Benzyl 4-bromo-3-fluorophenylcarbamate (20 g, 61.7 mmol) was dissolved in 180 mL THF, cooled to -78° C., and LiHMDS (1.0M in THY, 62.4 mL, 62.4 mmol) was added dropwise within 45 min.
After continued to stir for 30 min, R-glycidyl butyrate (2.21 mL, 62.3 mmol) was added dropwise.
After continued to react for 1 h at low temperature, it was warmed to room temperature and reacted for 60 h.
The reaction was quenched with saturated ammonium chloride.
Water was added, and extracted with ethyl acetate.
The organic phase was dried, concentrated, and then separated by a silica gel column (petroleum ether:ethyl acetate=2:1) to obtain 8.1 g of (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one, at a yield of 45.3percent.

Reference: [1] Patent: EP2692727, 2014, A2, . Location in patent: Paragraph 0161-0162
[2] Patent: US2014/179691, 2014, A1, . Location in patent: Paragraph 0172-0174
[3] Patent: US9133213, 2015, B2, . Location in patent: Page/Page column 28; 29
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5310 - 5321
[5] Patent: WO2015/66413, 2015, A1, . Location in patent: Page/Page column 141; 142
[6] Patent: EP2762480, 2014, A1, . Location in patent: Paragraph 0090; 0091
[7] Patent: US2014/243288, 2014, A1, . Location in patent: Paragraph 0172; 0173
[8] Patent: WO2017/66964, 2017, A1, . Location in patent: Page/Page column 37
  • 2
  • [ 656-65-5 ]
  • [ 501-53-1 ]
  • [ 510729-01-8 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate In acetone at 15 - 22℃; for 1.5 h; Sodium hydrogen carbonate (27.63 g, 0.329 mol, 1.25 eq) and a saturated solution of sodium hydrogen carbonate (333 ml) were added to a stirred solution of 4-bromo-3-fluoroaniline (50.0 g, 0.263 mol, 1 eq) in acetone (660 ml).
The resulting mixture was cooled to 15° C. and benzyl chloroformate (39 ml, 0.276 mol, 1.05 eq) was added gradually, taking care that the reaction temperature did not exceed 22° C.
The mixture was stirred over 90 mins at room temperature and the acetone was removed under vacuum.
The aqueous layer was then extracted with ethyl acetate (3*150 ml).
The combined organic layers were then washed with a saturated sodium chloride solution, and dried over MgSO4.
After filtration, the solvent was removed, and n-hexane added.
The mixture was stirred during 30 min at room temperature, the crystals were filtrated and washed with hexane to give the first crop of solid.
The filtrate was evaporated, and the solid mixed with heptane at 0° C. and stirred during 30 min.
The product was again filtered, to give the second crop of solid.
The two crops were then combined, to give the product (85.3 g, quantitative) as of solid.
100%
Stage #1: With sodium hydrogencarbonate In tetrahydrofuran at 0℃; for 0.0833333 h;
Stage #2: at 0℃; for 3 h;
General procedure: The desired aniline (1 mmol) was dissolved in THF (4 mL), then NaHCO3 (2 mmol) was added and the mixture was cooled to 0 °C.  After 5 min, benzyl chloroformate (0.17 mL, 1.2 mmol) was added drop wise and the mixture was continuously stirred at 0 °C for 3 hrs. The reaction mixture was then diluted with DDW (10 ml) followed by extraction with EtOAc (3× 25 mL). The combined organic layers were washed with brine then dried over Na2SO4, filtered and concentrated under vacuum.
94% With sodium hydrogencarbonate In water; acetone at 0 - 20℃; for 24 h; 4-bromo-3-fluoroaniline (2.5 g, 13.1 mmol, 1.0 equiv) was dissolved in acetone: water (2:1, 30 mL) and the solution was cooled to 0°C. NaHCO3 (2.20 g, 26.3 mmol, 2.0 equiv), CBZ-Cl (2.68 g, 15.8 mmol, 1.2 equiv) were added and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford product 3.4.1a (4.0 g, 94 percent yield). LCMS (mlz): 322.1 [M-2]. 1H NMR (400 MHz, DMSO) 6 10.17(s, 1H), 7.65—7.51 (m, 2H), 7.48—7.32(m, 5H), 7.27—7.17(m, 1H), 5.17(s, 2H).
92% With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 2.16667 h; cooling with ice To a 12-L, three-neck, round-bottom flask equipped with an overhead stirrer, nitrogen inlet/outlet, addition funnel and thermocouple was charged 4-bromo-3- fluoroaniline (800.0 g, 4.21 mol, Matrix lot No. Q13H), THF (6.4 L, 8 vol), and solid sodium bicarbonate (530.5 g, 6.32 mol, 1.5 eq). The addition funnel was charged with benzyl chloroformate (861.9 g, 5.05 mol, 1.2 eq), which was added dropwise to the reactor over 70 minutes. The temperature of the reaction was maintained below 200C with an ice water bath. The batch was aged 1 hour at room temperature at which point HPLC analysis indicated that the reaction was complete. The reaction mixture was transferred to a 22-L flask and the mixture was diluted with water (6.4 L, 8 vol). The two-phase mixture was warmed to 50°C and held at temperature for 16 hours to quench the excess benzyl chloroformate. The mixture was transferred hot to a separatory funnel to remove the lower aqueous phase. A rag layer was observed which was taken with the aqueous layer. The THF layer was filtered through Whatman No.1 filter paper to remove some particulates, and the mixture was transferred back to a 22-L flask equipped for distillation. Heptane was added in portions and distilled to remove the THF. (Note that it is best to distill some of the THF out first before adding the first amount of heptane.) A total of 26.5 L of heptane was added, and the total distillate collected was 25 L. At this point, the pot temperature had reached 97.7°C and the distillate coming over contained 0.9percent THF by 1H NMR analysis. The mixture was cooled to room temperature and the thick white slurry was filtered. The filter cake was washed with heptane (4 L). The product was dried in a vacuum oven at 400C to give 1257.0 g of intermediate 5 (92percent yield). The HPLC assay was 98.3percent (AUC).
173 g With sodium hydroxide In dichloromethane at 20℃; for 1 h; 100 g (528 mmol) of 3-fluoro-4-bromoaniline was dissolved in 500 mL of dichloromethane, 800 mL of an aqueous 1N NaOH solution was added thereto, and 82 mL (580 mmol) of Cbz-Cl (benzyl chloroformate) was slowly added dropwise thereto while stirring the resulting solution. The resulting solution was stirred at room temperature for 1 hour to separate an organic layer therefrom. The organic layer was washed twice with water, dehydrated using anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 173 g (528 mmol) of Compound XXIX as a white solid. [0159] 1H NMR (600 MHz, CDCl3) δ 7.40 (m, 7H), 6.93 (dd, J1 = 9.0 Hz, J2 = 2.4 Hz, 1H), 6.71 (s, 1H), 5.20 (s, 2H)
173 g With sodium hydroxide In dichloromethane; water at 20℃; Preparation of Compound XXIX 100 g (528 mmol) of 3-fluoro-4-bromoaniline was dissolved in 500 mL of dichloromethane, 800 mL of an aqueous 1N NaOH solution was added thereto, and 82 mL (580 mmol) of Cbz-Cl (benzyl chloroformate) was slowly added dropwise thereto while stirring the resulting solution. The resulting solution was stirred at room temperature for 1 hour to separate an organic layer therefrom. The organic layer was washed twice with water, dehydrated using anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 173 g (528 mmol) of Compound XXIX as a white solid. [0171] 1H NMR (600 MHz, CDCl3) δ 7.40 (m, 7H), 6.93 (dd, J1=9.0 Hz, JZ=2.4 Hz, 1H), 6.71 (s, 1H), 5.20 (s, 2H)

Reference: [1] Patent: US9133213, 2015, B2, . Location in patent: Page/Page column 28
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5310 - 5321
[3] Patent: WO2015/66413, 2015, A1, . Location in patent: Page/Page column 141; 142
[4] Patent: WO2010/42887, 2010, A2, . Location in patent: Page/Page column 16-17
[5] Patent: EP2692727, 2014, A2, . Location in patent: Paragraph 0158-0159
[6] Patent: US2014/179691, 2014, A1, . Location in patent: Paragraph 0169-0171
[7] Patent: CN103360379, 2017, B, . Location in patent: Paragraph 0072-0073
  • 3
  • [ 1056039-83-8 ]
  • [ 510729-01-8 ]
  • [ 1220910-89-3 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In water at 80℃; for 12 h; Inert atmosphere Compound 2 (120g, 0.5mol), potassium acetate (145g, 0.5mol) and frequencymellow joint boron is (150g, 0.6mol) 10L in four-mouth bottle, by adding 1,4-dioxane (3L) and Pd (dppf)2Cl2·CH2Cl2(20g, 25mmol). After the protection of nitrogen, heating to 80 °C, reaction 3 hours. Combined liquid detection for determining compound 2 is fully converted to compound 3 the rear, the compound is added 4 (146g, 0.45mol), potassium carbonate (173g, 1.2mol) and water (1L), re-protection of nitrogen, heating to 80 °C reaction 12 hours. LCMS determining the reaction is complete. Filtering, filtering the solid material, the filtrate obtained by reducing pressure and evaporating the evaporimeter 1,4-dioxane, is added to the aqueous phase 500 ml ethanol, beating sleepovers. Filtering, the filter cake is washed with cold-b activity, reduced-pressure drying 4 hours. The crude product in ethyl acetate, heating reflow, holding 5 minutes, the heat filters. Then reducing the temperature to room temperature, the beating sleepovers, filtering, washing the filter cake by ethyl acetate, to obtain compound 1 (177g, 88percent), yellow solid.
Reference: [1] Patent: CN105367547, 2016, A, . Location in patent: Paragraph 0034; 0035; 0036
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