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Product Details of [ 3430-17-9 ]

CAS No. :3430-17-9 MDL No. :MFCD00239380
Formula : C6H6BrN Boiling Point : -
Linear Structure Formula :NC5H3(CH3)Br InChI Key :PZSISEFPCYMBDL-UHFFFAOYSA-N
M.W : 172.02 Pubchem ID :220832
Synonyms :
2-Bromo-3-picoline

Calculated chemistry of [ 3430-17-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.9
TPSA : 12.89 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) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 2.24
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.231 mg/ml ; 0.00134 mol/l
Class : Soluble
Log S (Ali) : -2.15
Solubility : 1.23 mg/ml ; 0.00714 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0948 mg/ml ; 0.000551 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 3430-17-9 ]

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

Application In Synthesis of [ 3430-17-9 ]

* 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 [ 3430-17-9 ]
  • Downstream synthetic route of [ 3430-17-9 ]

[ 3430-17-9 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 3430-17-9 ]
  • [ 74-88-4 ]
  • [ 583-61-9 ]
Reference: [1] Australian Journal of Chemistry, 2013, vol. 66, # 2, p. 199 - 207
  • 2
  • [ 3430-17-9 ]
  • [ 68-12-2 ]
  • [ 55589-47-4 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 4, p. 1247 - 1252
  • 3
  • [ 3430-17-9 ]
  • [ 1603-40-3 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 6, p. 925 - 927
  • 4
  • [ 1603-40-3 ]
  • [ 3430-17-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Tetrahedron, 2015, vol. 71, # 2, p. 252 - 258
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2002, vol. 177, # 11, p. 2579 - 2587
[4] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 3126
[6] Journal of the Chemical Society, 1949, p. 2094
[7] Organic Magnetic Resonance, 1982, vol. 20, # 4, p. 242 - 248
[8] Gazzetta Chimica Italiana, 1983, vol. 113, # 3/4, p. 227 - 228
[9] Journal of Organic Chemistry, 1998, vol. 63, # 20, p. 6886 - 6890
[10] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6033 - 6036
  • 5
  • [ 1003-56-1 ]
  • [ 3430-17-9 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 6
  • [ 13534-89-9 ]
  • [ 74-88-4 ]
  • [ 3430-17-9 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 5, p. 1110 - 1113
[2] Australian Journal of Chemistry, 2013, vol. 66, # 2, p. 199 - 207
  • 7
  • [ 13534-89-9 ]
  • [ 74-88-4 ]
  • [ 109-04-6 ]
  • [ 3430-17-9 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 5, p. 1110 - 1113
[2] Green Chemistry, 2011, vol. 13, # 5, p. 1110 - 1113
  • 8
  • [ 109-04-6 ]
  • [ 74-88-4 ]
  • [ 3430-17-9 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1982, # 10, p. 2863 - 2878
  • 9
  • [ 626-05-1 ]
  • [ 74-88-4 ]
  • [ 3430-17-9 ]
Reference: [1] Journal of Organometallic Chemistry, 1990, vol. 382, # 3, p. 319 - 332
  • 10
  • [ 3430-17-9 ]
  • [ 42753-71-9 ]
YieldReaction ConditionsOperation in experiment
90.1% With sodium amide In 5,5-dimethyl-1,3-cyclohexadiene at 118 - 120℃; for 1 h; Inert atmosphere Example 2
To the reaction tank was charged 650g of xylene as a solvent, heated up to 115 ~ 120 deg. C heated under reflux until complete removal of the water; under nitrogen, the solvent was cooled to 70 deg. C, sodium amide was added 22g, and then the solution was heated to 118 to 120 deg. C, was added dropwise under reflux 102g of 2-bromo-3-methylpyridine, the addition was complete, the reaction maintaining the temperature at reflux 1H; After the reaction, the reaction solution was cooled to 45 deg. C, and then poured into ice water, separation of the upper solvent layer; xylene was concentrated at atmospheric pressure, the remaining 220g, stirring cooling to 10 ~ 15 deg. C, crystallization give the desired product 2- methyl-6-amino-5-bromopyridine 100g, content 99.3percent, yield 90.1percent.
Reference: [1] Patent: CN105348181, 2016, A, . Location in patent: Paragraph 0023; 0024; 0025
  • 11
  • [ 3430-17-9 ]
  • [ 124-38-9 ]
  • [ 4021-07-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 2, p. 216 - 223
  • 12
  • [ 3430-17-9 ]
  • [ 19230-57-0 ]
YieldReaction ConditionsOperation in experiment
60% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 12 h; To a stirred solution of 2-bromo-3-methylpyridine (50g) in dichloromethane (500mL) was added 3-chloroperbenzoic acid (bOg) at about room temperature. The reactionmixture was stirred for about 1 2h at about room temperature and was filtered. The filtrate was quenched in to saturated sodium thiosulfate solution. The reaction mixture was stirred for about lh at about room temperature. The two layers were separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layer was washed with water and saturated brine solution, dried and concentrated underreduced pressure at about 40°C. The solid was purified by column chromatography (5-7percent methanol in ethyl acetate). Yield: 33g (60percent)‘H NMR (300MHz, CDC13): ö 8.30-8.29 (m,1H), 7.14-7.12(m,2H), 2.47 (s,3H)IR: 3382, 3051, 1670, 1436, 1410, 1275, 1240, 1067, 958, 786, 695, 599 cmMass [M+H] : 188.09
47% With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid In dichloromethane; ethyl acetate EXAMPLE 89A
2-bromo-3-methylpyridine 1-oxide
A solution of 2-bromo-3-methylpyridine (10.0 mL, 0.0898 mol) in dichloromethane (150 mL) at 0° C. was treated with mCPBA (~77percent, 22.1 g, 0.0987 mol) in three equivalent portions.
The mixture was warmed to room temperature, stirred for 18 hours, cooled to 0° C., and treated with 1N NaOH (50 mL).
The organic phase was washed with 1N NaOH and saturated NaHCO3, dried (MgSO4), filtered, and concentrated.
The concentrate was purified by flash column chromatography on silica gel with ethyl acetate and 9:1 ethyl acetate/methanol to provide 7.83 g (47percent) of the desired product. MS (DCI/NH3) m/z 187.9 (M+H)+; 1H NMR (CDCl3) δ8.28-8.26 (m, 1H), 7.15-7.09 (m, 2H), 2.46 (s, 3H).
47% With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid In dichloromethane; ethyl acetate EXAMPLE 89A
2-bromo-3-methylpyridine 1-oxide
A solution of 2-bromo-3-methylpyridine (10.0 mL, 0.0898 mol) in dichloromethane (150 mL) at 0° C. was treated with mCPBA (~77percent, 22.1 g, 0.0987 mol) in three equivalent portions.
The mixture was warmed to room temperature, stirred for 18 hours, cooled to 0° C., and treated with 1N NaOH (50 mL).
The organic phase was washed with 1N NaOH and saturated NaHCO3, dried (MgSO4), filtered, and concentrated.
The concentrate was purified by flash column chromatography on silica gel with ethyl acetate and 9:1 ethyl acetate/methanol to provide 7.83 g (47percent) of the desired product. MS (DCI/NH3) m/z 187.9 (M+H)+; 1H NMR (CDCl3) δ 8.28-8.26 (m, 1H), 7.15-7.09 (m, 2H), 2.46 (s, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 16, p. 7126 - 7135
[2] Patent: WO2017/56031, 2017, A1, . Location in patent: Paragraph 0164
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 9, p. 1571 - 1574
[4] Patent: US2003/87940, 2003, A1,
[5] Patent: US2002/115640, 2002, A1,
[6] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 16, p. 6106 - 6122
[7] Patent: WO2017/175161, 2017, A1, . Location in patent: Page/Page column 49
  • 13
  • [ 3430-17-9 ]
  • [ 35905-85-2 ]
YieldReaction ConditionsOperation in experiment
62% With potassium permanganate In water for 5 h; Heating / reflux 2-bromo-3-methylpyridine (25.0 mL, 213 mmol) was added to a solution of potassium permanganate (87.7 g, 555 mmol) in 800 ML of water and the mixture was stirred under reflux. After 5 hours, 600 mL of water was distilled off and the remaining suspension was filtered. The residue was washed with two 50 mL portions of hot water and the combined filtrates were acidified with concentrated HC1. The white precipitate was filtered and dried in a vacuum oven to give 26.8 g of 2-bromonicotinic acid (62percent yield). DIPHENYLPHOSPHORYLAZIDE was added to a solution of 2-bromonicotinic acid (15.0 g, 74.0 mmol) and triethylamine (11.4 mL, 81. 4 mmol) in 140 mL of anhydrous tert-butanol. The reaction mixture was stirred under reflux for 2 hours, cooled to room temperature, and concentrated in VACUO. The residue was dissolved in 150 ML of ethyl acetate and washed with three 50 mL portions of water, three 50 mL portions of saturated aqueous sodium bicarbonate, and with two 50 mL portions of brine. The organic layer was dried over magnesium sulfate (MGS04), filtered, and concentrated in vacuo. The residue crystallized upon standing to give 15.3 g of the title product (76percent yield).
Reference: [1] Organic Letters, 2007, vol. 9, # 5, p. 891 - 894
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Patent: WO2005/30213, 2005, A1, . Location in patent: Page/Page column 165
[4] Tetrahedron, 2015, vol. 71, # 2, p. 252 - 258
[5] Journal of Organic Chemistry, 1949, vol. 14, p. 509,513
[6] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 5, p. 641 - 645
[7] Synthesis, 2003, # 4, p. 551 - 554
[8] Patent: US6060491, 2000, A,
  • 14
  • [ 3430-17-9 ]
  • [ 52718-95-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 5, p. 641 - 645
[2] Journal of Organic Chemistry, 1949, vol. 14, p. 509,513
  • 15
  • [ 3430-17-9 ]
  • [ 89466-17-1 ]
Reference: [1] Patent: WO2017/56031, 2017, A1,
[2] Patent: WO2017/56031, 2017, A1,
  • 16
  • [ 3430-17-9 ]
  • [ 89466-17-1 ]
Reference: [1] Patent: WO2017/175161, 2017, A1,
  • 17
  • [ 3430-17-9 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 59718-84-2 ]
YieldReaction ConditionsOperation in experiment
93.6% at 80℃; for 16 h; A mixture of 2-bromo-3-methylpyridine (5.0 g, 29.0 mmol), Pd(dppf)C12 (2.1 g, 2.9 mmol), and triethylamine (8.8 g, 87 mmol) in methanol (250 mL) was stirred at 80 °C under CO atmosphere (50 psi) for 16 h. The mixture was filtered and the filtrate concentrated in vacuo, then purified by column chromatography on Si02 to give the desired product (4.1 g, 93.6percent). LCMS (mlz): 152.0 (M+1).
Reference: [1] Patent: WO2015/200677, 2015, A2, . Location in patent: Paragraph 00470; 00471
  • 18
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  • [ 59718-84-2 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 9, p. 2930 - 2934
  • 19
  • [ 3430-17-9 ]
  • [ 1003-56-1 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With potassium <i>tert</i>-butylate In tert-Amyl alcohol at 100℃; for 40 h; Schlenk technique; Inert atmosphere
Stage #2: at 20℃; for 24 h;
General procedure: In a dry Schlenk tube 2-bromo-6-methylpyridine (5.98 g, 35.0 mmol) was dissolved in 100 mL oft-AmylOH and KOt-Bu (39.3 g , 350.0 mmol) was added. The mixture was stirred at 100 °C for 40 h. The solvent was removed under reduced pressure and the residue was dissolved in 50 mL of HCO2H. The solution was stirred for 24 h at rt, then the pH was set to about 6 using 3N aq. KOH solution. The extraction was performed using CHCl3 (3×) and the combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated. The residue was transferred to a column chromatography (8percentMeOH in DCM) to afford 1 (white solid), 2.75 g (72percent).
Reference: [1] Synlett, 2015, vol. 26, # 11, p. 1557 - 1562
  • 20
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  • [ 128071-75-0 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 5, p. 891 - 894
[2] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6033 - 6036
[3] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[4] Synthetic Communications, 2013, vol. 43, # 23, p. 3175 - 3180
[5] European Journal of Medicinal Chemistry, 2014, vol. 83, p. 709 - 716
  • 21
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  • [ 116308-35-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 22
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  • [ 131747-57-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 23
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  • [ 131747-43-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
  • 24
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  • [ 116986-09-5 ]
Reference: [1] Patent: WO2015/200677, 2015, A2,
  • 25
  • [ 3430-17-9 ]
  • [ 94446-97-6 ]
YieldReaction ConditionsOperation in experiment
41% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 40℃; for 8 h; UV-irradiation; Inert atmosphere This intermediate was generated by a modified procedure based on thatdisclosed in Rebek, J., et al., I Am. Chem. Soc., 107, 7487 (1985)). A three-neckround bottom flask with a stir bar was flame dried, cooled under vacuum and purged with N2. To the flask were added 2-bromo-3-methylpyndine (5.2 mL, 29.1 mmol), N-bromosuccinimide (5.5 g, 32.0 mmol), and degassed benzene (126 mL). The flask was fitted with a condenser, heated to 40 °C and AIBN (0.24 g, 1.5 mmol) was addedin several portions. The reaction was irradiated using a sun lamp as it was stirred at40 °C. The reaction was monitored using TLC and HPLC and was stopped after 80percentconversion of the pyridine reagent (approximately 8 hrs). The reaction wasconcentrated under reduced pressure, then redissolved in 4:1 DCM/EtOAc (120 mL)and extracted once with 50 mL of a saturated solution of NaHCO3(aq), water and asaturated solution of NaCl(aq). The organic phase was dried over anhydrous sodiumsulphate, filtered and concentrated. Upon standing the residue could not be fully redissolved in DCM and the resultant suspension was filtered to remove the insoluble solid. The filtrate was concentrated to near dryness and the residue was purified by normal phase flash chromatography (EtOAc/Hexanes) to give the title compound I-i(3.0 g, 11.9 mmol, 41percent) as a yellow solid. ‘H NMR (400 MHz, CDC13) ö 8.33 (1H, dd, J5,2 Hz), 7.78 (1H, dd, J7,2 Hz), 7.28 (1H, dd, J=5,4 Hz), 4.57 (2H, s), MS (LC/MS) m/z observed 249.97, expected 249.89 [M+Hj
41% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 40℃; for 8 h; Inert atmosphere; Irradiation This intermediate was generated by a modified procedure based on that disclosed in Rebek, J., et al., J Am. Chem. Soc., 107, 7487 (1985)). A three-neck round bottom flask with a stir bar was flame dried, cooled under vacuum and purged with N2. To the flask were added 2-bromo-3-methylpyridine (5.2 ml, 29.1 mmol), N-bromosuccinimide (5.5 g, 32.0 mmol), and degassed benzene (126 ml). The flask was fitted with a condenser, heated to 40°C and AIBN (0.24 g, 1.5 mmol) was added in several portions. The reaction was irradiated using a sun lamp as it was stirred at 40°C.The reaction was monitored using TLC and HPLC and was stopped after 80percent conversion of the pyridine compound (approximately 8 hrs). The reaction was concentrated under reduced pressure, then redissolved in DCM/EtOAc (120 ml, 4:1 (v/v)) and extracted once with 50 ml of NaHCO3 (satd, aqueous) water and brine. The organic phase was dried over anhydrous sodium sulphate, filtered and concentrated. Upon standing the residue could not be fully redissolved in DCM and the resultant suspension was filtered to remove the insoluble solid. The filtrate was concentrated to near dryness and the residue was purified by normal phase flash chromatography (EtOAc/Hexanes) to give the title compound I-4 (3.0 g, 11.9 mmol, 41percent) as a yellow solid. H1 NMR (400 MHz, CDCl3) δ 8.33(1H, dd, J=5.2 Hz), 7.78(1H, dd, J=7.2 Hz), 7.28(1H, dd, J=5.4 Hz), 4.57(2H, s), MS (EC/MS) m/z observed 249.97, expected 249.89 [M+H].
34% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3 h; Reflux A mixture of 2-bromo-3-methylpyridine (2.0 mL, 17.9mmoli), NBS (3.5 g,19.7 mmoli) and benzoyl peroxide (1.8 g, 10.2 mmoli) in CCl4 (180 mL) was refluxed for 3 h. After cooling, the mixture was poured into H2O (100 mL) and extracted with CHCl3 (3 x 50 ml). The organic phase was evaporated under reduced pressure and purified by column chromatography (eluting with CE/EtOAc 8/2) to give 2-bromo-3-bromomethylpyridine (yield34percent), as an oil; 1H NMR (300 MHz, DMSO-d6): δ 8.35 (dd, J= 4.7 and 1.7 Hz, 1 H, 6-H); 8.05 (dd, J= 7.5 and 1.7 Hz, 1 H, 4-H); 7.49 (dd, J = 7.5 and 4.7 Hz, 1 H, 5-H); 4.72 (s,2 H, CH2Br).
Reference: [1] Journal of the American Chemical Society, 1985, vol. 107, # 25, p. 7487 - 7493
[2] Heterocycles, 1984, vol. 22, # 10, p. 2191 - 2194
[3] Patent: WO2016/15159, 2016, A1, . Location in patent: Page/Page column 55
[4] Patent: US9458192, 2016, B1, . Location in patent: Page/Page column 44
[5] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 559 - 564
[6] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 416 - 425
[7] Journal of Medicinal Chemistry, 2009, vol. 52, # 17, p. 5323 - 5329
[8] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4721 - 4736
[9] Journal of Organic Chemistry, 2001, vol. 66, # 18, p. 6083 - 6091
[10] Journal of Medicinal Chemistry, 2007, vol. 50, # 23, p. 5752 - 5764
[11] Patent: WO2007/53435, 2007, A1, . Location in patent: Page/Page column 20
[12] Patent: WO2008/9122, 2008, A1, . Location in patent: Page/Page column 125
[13] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5071 - 5074
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  • [ 450844-27-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 9, p. 1571 - 1574
  • 27
  • [ 3430-17-9 ]
  • [ 1461-22-9 ]
  • [ 259807-97-1 ]
YieldReaction ConditionsOperation in experiment
27%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78℃; for 1 h;
To 2-bromo-3-methylpyridine (1.3 mE, 11.7 mmol) in THF (35 mE) at —78° C. was added n-BuEi (2.5 M in hexanes, 5.6 mE, 14 mmol). Afier 30 mi tri-n-butyltin chloride (3.8 mE, 14 mmol) was added. After 1 hat —78° C., the reaction was allowed to warm to rt. EtOAc was added and the reaction mixture was washed with 10percent aq KF. The organic layer was dried (Mg504). Purification via silica gel chromatography (0-15percent EtOAc in heptane) gave the title compound (1.2 g, 27percent). MS (ESI) mass calcd. for C18H33NSn, 382.2; mlz found 384.0 [M+H].
Reference: [1] Patent: US2016/46640, 2016, A1, . Location in patent: Paragraph 0332
  • 28
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  • [ 1083057-14-0 ]
Reference: [1] Patent: US2013/186801, 2013, A1,
[2] Patent: WO2013/185112, 2013, A1,
[3] Patent: WO2014/71122, 2014, A1,
[4] Patent: WO2015/73231, 2015, A1,
[5] Patent: US2015/231142, 2015, A1,
[6] Patent: US9241934, 2016, B2,
[7] Patent: US2016/324788, 2016, A1,
[8] Patent: US2011/98311, 2011, A1,
[9] Patent: WO2018/107100, 2018, A1,
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