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[ CAS No. 1103738-30-2 ] {[proInfo.proName]}

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Chemical Structure| 1103738-30-2
Chemical Structure| 1103738-30-2
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Product Details of [ 1103738-30-2 ]

CAS No. :1103738-30-2 MDL No. :MFCD25977360
Formula : C23H25ClO6 Boiling Point : -
Linear Structure Formula :- InChI Key :TUBVOYXRJBKZBN-MLNNCEHLSA-N
M.W : 432.89 Pubchem ID :57558247
Synonyms :

Calculated chemistry of [ 1103738-30-2 ]

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.43
Num. rotatable bonds : 6
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 111.47
TPSA : 74.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.9
Log Po/w (XLOGP3) : 4.54
Log Po/w (WLOGP) : 3.75
Log Po/w (MLOGP) : 2.23
Log Po/w (SILICOS-IT) : 4.4
Consensus Log Po/w : 3.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.28
Solubility : 0.00225 mg/ml ; 0.0000052 mol/l
Class : Moderately soluble
Log S (Ali) : -5.82
Solubility : 0.000654 mg/ml ; 0.00000151 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.18
Solubility : 0.000288 mg/ml ; 0.000000665 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.62

Safety of [ 1103738-30-2 ]

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

Application In Synthesis of [ 1103738-30-2 ]

* 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 [ 1103738-30-2 ]
  • Downstream synthetic route of [ 1103738-30-2 ]

[ 1103738-30-2 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 461432-23-5 ]
  • [ 1103738-19-7 ]
  • [ 1103738-30-2 ]
YieldReaction ConditionsOperation in experiment
86.3%
Stage #1: With n-butyllithium In tetrahydrofuran at -80 - -70℃; for 1 h;
Stage #2: at -80 - 0℃;
Add Compound C-1 (10 g, 30.7 mmol) to a 250 mL three-necked flaskAnd 70mL of tetrahydrofuran, stir and dissolve.The resulting solution is cooled to -70 to -80 ° C,Slowly add n-butyllithium solution (2.5M THF solution) to the cooled solution.14.1 mL, 1.15 eq), and stirred at -70 to -80 ° C for 1 hour.Further, a solution of the compound B in tetrahydrofuran (9.6 g of B in 30 mL of tetrahydrofuran, 35.3 mmol, 1.15 eq) was added dropwise to the reaction mixture.The mixture was stirred at -70 to -80 ° C for 2 hours. The reaction solution is heated to -10 to 0 ° C.The reaction solution was diluted with a saturated aqueous solution of NH4Cl (20 mL).The reaction quenching solution was extracted twice by adding ethyl acetate (100 mL×2).The ethyl acetate layer was combined and washed with brine (100 mL).The organic layer was concentrated to dryness under reduced pressure at 40 to 50 °C. The obtained solid was recrystallized from ethyl acetate and n-hexane to give 11.5 g of compound.D-1, yield 86.3percent.
Reference: [1] Patent: CN108675976, 2018, A, . Location in patent: Paragraph 0083; 0084; 0085
  • 2
  • [ 1103738-29-9 ]
  • [ 1103738-19-7 ]
  • [ 1103738-30-2 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at -5℃; for 3 h; Industry scale
Stage #2: With tert-butylmagnesium chloride In tetrahydrofuran at -25 - -20℃; for 3.68333 h; Industry scale
To a 20 L reactor equipped with a mechanical stirrer, a temperature controller and a nitrogen inlet was charged with the iodide (3.00 kg, 8.05 mol) and THF (8 L, 4.x. to the morpholinoamide) at room temperature and cooled to -5° C. To the above solution was added dropwise a solution of i-PrMgCl in THF (Aldrich 2 M, 4.39 L, 8.82 mol) at -5° C. over 3 hours. This Grignard solution was used in the ketone formation below.To a 50 L reactor equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged the morpholinoamide (HPLC purity=97 wt percent, 2.01 kg, 7.34 mol) and THF (11 L, 5.5.x.) at room temperature and stirred for 45 minutes at room temperature and for 15 minutes at 30° C. The homogeneous solution was then cooled to -25° C. To this solution was added a solution of t-BuMgCl in THF (Aldrich 1 M, 7.32 L, 7.91 mol) at -25° C. over 3 hours. Then the above Grignard solution was added to this solution at -20 over 41 minutes. The resulting solution was further stirred at -20° C. before quench. The reaction mixture was added to 10 wt percent aqueous NH4Cl (10 L, 5.x.) at 0° C. with vigorous stirring, and stirred for 30 minutes at 0° C. To this mixture was added slowly 6 N HCl (4 L, 2.x.) at 0° C. to obtain a clear solution and stirred for 30 minutes at 10° C. After phase split, the organic layer was washed with 25 wt percent aq NaCl (5 L, 2.5.x.). Then the organic layer was concentrated to a 3.x. solution under the conditions (200 mbar, bath temp 50° C.). EtOAc (24 L, 12.x.) was added, and evaporated to a 3.x. solution under the conditions (150 mbar, bath temp 50° C.). After removed solids by a polish filtration, EtOAc (4 L, 2.x.) was added and concentrated to dryness (150 mbar, bath temp 50° C.). The wet cake was then transferred to a 50 L reactor equipped with a mechanical stirrer, a temperature controller and a nitrogen inlet. After EtOAc was added, the suspension was heated at 70° C. to obtain a 2.5.x. homogeneous solution. To the resulting homogeneous solution was added slowly heptane (5 L, 2.5.x.) at the same temperature. A homogeneous solution was seeded and heptane (15 L, 7.5.x.) was added slowly to a little cloudy solution at 70° C. After stirred for 0.5 h at 70° C., the suspension was slowly cooled to 60° C. and stirred for 1 h at 60° C. The suspension was then slowly cool to room temperature and stirred for 14 h at the same temperature. The crystals were collected and washed with heptane (8 L, 4.x.), dried under vacuum at 45° C. to give the desired ketone as fluffy solids (2.57 kg, 100 wt percent by HPLC, purity-adjusted yield: 81percent).
81%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at -5℃; for 3 h; Industry scale
Stage #2: With tert-butylmagnesium chloride In tetrahydrofuran at -25 - -20℃; Industry scale
6.5. Alternative synthesis of (4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanone To a 20 L reactor equipped with a mechanical stirrer, a temperature controller and a nitrogen inlet was charged with the iodide (3.00 kg, 8.05 mol) and THF (8 L, 4X to the morpholinoamide) at room temperature and cooled to -5°C. To the above solution was added dropwise a solution of i-PrMgCl in THF (Aldrich 2 M, 4.39 L, 8.82 mol) at -5°C over 3 hours. This Grignard solution was used in the ketone formation below. To a 50 L reactor equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged the morpholinoamide (HPLC purity = 97 wtpercent, 2.01 kg, 7.34 mol) and THF (11 L, 5.5X) at room temperature and stirred for 45 minutes at room temperature and for 15 minutes at 30°C. The homogeneous solution was then cooled to - 25°C. To this solution was added a solution of t-BuMgCl in THF (Aldrich 1 M, 7.32 L, 7.91 mol) at -25°C over 3 hours. Then the above Grignard solution was added to this solution at -20 over 41 minutes. The resulting solution was further stirred at -20°C before quench. The reaction mixture was added to 10 wtpercent aqueous NH4Cl (10 L, 5X) at 0°C with vigorous stirring, and stirred for 30 minutes at 0°C. To this mixture was added slowly 6 N HCl (4 L, 2X) at 0°C to obtain a clear solution and stirred for 30 minutes at 10°C. After phase split, the organic layer was washed with 25 wtpercent aq NaCl (5 L, 2.5X). Then the organic layer was concentrated to a 3X solution under the conditions (200 mbar, bath temp 50°C). EtOAc (24 L, 12X) was added, and evaporated to a 3X solution under the conditions (150 mbar, bath temp 50°C). After removed solids by a polish filtration, EtOAc (4 L, 2X) was added and concentrated to dryness (150 mbar, bath temp 50°C). The wet cake was then transferred to a 50 L reactor equipped with a mechanical stirrer, a temperature controller and a nitrogen inlet. After EtOAc was added, the suspension was heated at 70°C to obtain a 2.5X homogeneous solution. To the resulting homogeneous solution was added slowly heptane (5 L, 2.5X) at the same temperature. A homogeneous solution was seeded and heptane (15 L, 7.5X) was added slowly to a little cloudy solution at 70°C. After stirred for 0.5 h at 70°C, the suspension was slowly cooled to 60°C and stirred for 1 h at 60°C. The suspension was then slowly cool to room temperature and stirred for 14 h at the same temperature. The crystals were collected and washed with heptane (8 L, 4X), dried under vacuum at 45°C to give the desired ketone as fluffy solids (2.57 kg, 100 wtpercent by HPLC, purity-adjusted yield: 81percent).
76% With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 4.5 h; To a solution of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (500 mg, 1.34 mmol) in THF (5.0 mL) was added i-PrMgCl (2.0M in THF, 1.0 mL, 2.00 mmol) at 0-5° C., and the mixture was stirred for 1.5 h at 0-5° C. A solution of (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone (146.5 mg, 0.536 mmol) in THF (1.0 mL) was added dropwise at 0-5° C. and the mixture was kept stirring for 1 h, warmed to 20° C. and stirred at 20° C. for 2 hours. The reaction was quenched with saturated aq NH4Cl, extracted with MTBE, washed with brine. The organic layer was concentrated and the residue was purified by silica gel column chromatography to afford the desired ketone (178 mg, 76percent) as a white solid. 1H NMR (CDCl3) δ 7.88 (dd, J=8.4, 2.0 Hz, 1H), 7.82 (d, J=2.0 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.12 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.07 (d, J=3.2 Hz, 1H), 5.21 (d, J=3.2 Hz, 1H), 4.58 (d, J=3.2 Hz, 1H), 4.56 (d, J=3.2 Hz, 1H), 4.16 (d, J=7.2 Hz, 2H), 4.03 (q, J=7.2 Hz, 2H), 1.54 (s, 3H), 1.42 (t, J=7.2 Hz, 3H), 1.37 (s, 3H).
76%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0 - 5℃; for 1.5 h;
Stage #2: at 0 - 20℃;
To a solution of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (500 mg, 1.34 mmol) in THF (5.0 mL) was added i-PrMgCl (2.0M in THF, 1.0 mL, 2.00 mmol) at 0-5° C., and the mixture was stirred for 1.5 h at 0-5° C. A solution of (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone (146.5 mg, 0.536 mmol) in THF (1.0 mL) was added dropwise at 0-5° C. and the mixture was kept stirring for 1 h, warmed to 20° C. and stirred at 20° C. for 2 hours. The reaction was quenched with saturated aq NH4Cl, extracted with MTBE, washed with brine. The organic layer was concentrated and the residue was purified by silica gel column chromatography to afford the desired ketone (178 mg, 76percent) as a white solid. 1H NMR (CDCl3) δ 7.88 (dd, J=8.4, 2.0 Hz, 1H), 7.82 (d, J=2.0 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.12 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.07 (d, J=3.2 Hz, 1H), 5.21 (d, J=3.2 Hz, 1H), 4.58 (d, J=3.2 Hz, 1H), 4.56 (d, J=3.2 Hz, 1H), 4.16 (d, J=7.2 Hz, 2H), 4.03 (q, J=7.2 Hz, 2H), 1.54 (s, 3H), 1.42 (t, J=7.2 Hz, 3H), 1.37 (s, 3H)
178 mg
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0 - 5℃; for 1.5 h;
Stage #2: at 0 - 20℃; for 3 h;
To a solution of 48 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (500mg, 1.34 mmol) in 20 THF (5.0 mL) was added 50 i-PrMgCl (2.0M in THF, 1.0 mL, 2.00 mmol) at 0-5°C, and the mixture was stirred for 1.5 h at 0-5°C. A solution of 13 (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone (146.5 mg, 0.536 mmol) in THF (1.0 mL) was added dropwise at 0-5°C and the mixture was kept stirring for 1h, warmed to 20°C and stirred at 20°C for 2 hours. The reaction was quenched with saturated aq NH4Cl, extracted with MTBE, washed with brine. The organic layer was concentrated and the residue was purified by silica gel column chromatography to afford the desired 51 ketone (178 mg, 76percent) as a white solid. 1H NMR (CDCl3) δ 7.88 (dd, J = 8.4, 2.0 Hz, 1H), 7.82 (d, J = 2.0 Hz, 1H), 7.50 (d, J = 8.4 Hz, 1H), 7.12 (d, J = 8.4 Hz, 2H), 6.86 (d, J = 8.4 Hz, 2H), 6.07 (d, J = 3.2 Hz, 1H), 5.21 (d, J = 3.2 Hz, 1H), 4.58 (d, J = 3.2 Hz, 1H), 4.56 (d, J = 3.2 Hz, 1H), 4.16 (d, J = 7.2 Hz, 2H), 4.03 (q, J = 7.2 Hz, 2H), 1.54 (s, 3H), 1.42 (t, J = 7.2 Hz, 3H), 1.37 (s, 3H).

Reference: [1] Patent: US2009/30198, 2009, A1, . Location in patent: Page/Page column 9-10
[2] Patent: EP2332947, 2011, A1, . Location in patent: Page/Page column 8
[3] Patent: US2009/30198, 2009, A1, . Location in patent: Page/Page column 9
[4] Patent: US2010/16422, 2010, A1, . Location in patent: Page/Page column 6
[5] Patent: EP2661256, 2018, B1, . Location in patent: Paragraph 0097
  • 3
  • [ 1103738-29-9 ]
  • [ 1103738-19-7 ]
  • [ 1103738-30-2 ]
YieldReaction ConditionsOperation in experiment
76% With i-PrMgCl In tetrahydrofuran 6.4.
Synthesis of (4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)methanone
To a solution of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (500 mg, 1.34 mmol) in THF (5.0 mL) was added i-PrMgCl (2.0M in THF, 1.0 mL, 2.00 mmol) at 0-5° C., and the mixture was stirred for 1.5 h at 0-5° C. A solution of (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone (146.5 mg, 0.536 mmol) in THF (1.0 mL) was added dropwise at 0-5° C. and the mixture was kept stirring for 1 h, warmed to 20° C. and stirred at 20° C. for 2 hours.
The reaction was quenched with saturated aq NH4Cl, extracted with MTBE, washed with brine.
The organic layer was concentrated and the residue was purified by silica gel column chromatography to afford the desired ketone (178 mg, 76percent) as a white solid. 1H NMR (CDCl3) δ 7.88 (dd, J=8.4, 2.0 Hz, 1H), 7.82 (d, J=2.0 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.12 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 6.07 (d, J=3.2 Hz, 1H), 5.21 (d, J=3.2 Hz, 1H), 4.58 (d, J=3.2 Hz, 1H), 4.56 (d, J=3.2 Hz, 1H), 4.16 (d, J=7.2 Hz, 2H), 4.03 (q, J=7.2 Hz, 2H), 1.54 (s, 3H), 1.42 (t, J=7.2 Hz, 3H), 1.37 (s, 3H).
Reference: [1] Patent: US2012/172320, 2012, A1,
  • 4
  • [ 677-22-5 ]
  • [ 1103738-30-2 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride; i-PrMgCl; nitrogen In tetrahydrofuran; n-heptane; ethyl acetate 6.5.
Alternative synthesis of (4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol-5-yl)methanone
To a 20 L reactor equipped with a mechanical stirrer, a temperature controller and a nitrogen inlet was charged with the iodide (3.00 kg, 8.05 mol) and THF (8 L, 4X to the morpholinoamide) at room temperature and cooled to -5° C.
To the above solution was added dropwise a solution of i-PrMgCl in THF (Aldrich 2 M, 4.39 L, 8.82 mol) at -5° C. over 3 hours.
This Grignard solution was used in the ketone formation below.
To a 50 L reactor equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged the morpholinoamide (HPLC purity=97 wt percent, 2.01 kg, 7.34 mol) and THF (11 L, 5.5X) at room temperature and stirred for 45 minutes at room temperature and for 15 minutes at 30° C.
The homogeneous solution was then cooled to -25° C.
To this solution was added a solution of t-BuMgCl in THF (Aldrich 1 M, 7.32 L, 7.91 mol) at -25° C. over 3 hours.
Then the above Grignard solution was added to this solution at -20 over 41 minutes.
The resulting solution was further stirred at -20° C. before quench.
The reaction mixture was added to 10 wt percent aqueous NH4Cl (10 L, 5X) at 0° C. with vigorous stirring, and stirred for 30 minutes at 0° C.
To this mixture was added slowly 6 N HCl (4 L, 2X) at 0° C. to obtain a clear solution and stirred for 30 minutes at 10° C.
After phase split, the organic layer was washed with 25 wt percent aq NaCl (5 L, 2.5X ).
Then the organic layer was concentrated to a 3X solution under the conditions (200 mbar, bath temp 50° C.). EtOAc (24 L, 12X) was added, and evaporated to a 3X solution under the conditions (150 mbar, bath temp 50° C.).
After removed solids by a polish filtration, EtOAc (4 L, 2X) was added and concentrated to dryness (150 mbar, bath temp 50° C.).
The wet cake was then transferred to a 50 L reactor equipped with a mechanical stirrer, a temperature controller and a nitrogen inlet.
After EtOAc was added, the suspension was heated at 70° C. to obtain a 2.5X homogeneous solution.
To the resulting homogeneous solution was added slowly heptane (5 L, 2.5X) at the same temperature.
A homogeneous solution was seeded and heptane (15 L, 7.5X) was added slowly to a little cloudy solution at 70° C.
After stirred for 0.5 h at 70° C., the suspension was slowly cooled to 60° C. and stirred for 1 h at 60° C.
The suspension was then slowly cool to room temperature and stirred for 14 h at the same temperature.
The crystals were collected and washed with heptane (8 L, 4X), dried under vacuum at 45° C. to give the desired ketone as fluffy solids (2.57 kg, 100 wt percent by HPLC, purity-adjusted yield: 81percent).
Reference: [1] Patent: US2012/172320, 2012, A1,
  • 5
  • [ 19094-56-5 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: EP2332947, 2011, A1,
[2] Patent: EP2661256, 2018, B1,
  • 6
  • [ 609-06-3 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: EP2332947, 2011, A1,
[2] Patent: EP2332947, 2011, A1,
[3] Patent: EP2661256, 2018, B1,
[4] Patent: EP2661256, 2018, B1,
  • 7
  • [ 114861-22-2 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: EP2332947, 2011, A1,
[2] Patent: EP2332947, 2011, A1,
[3] Patent: EP2661256, 2018, B1,
[4] Patent: EP2661256, 2018, B1,
  • 8
  • [ 1103738-17-5 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: EP2332947, 2011, A1,
[2] Patent: CN108675976, 2018, A,
[3] Patent: EP2661256, 2018, B1,
  • 9
  • [ 281652-58-2 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: EP2332947, 2011, A1,
[2] Patent: EP2661256, 2018, B1,
  • 10
  • [ 1103738-26-6 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: EP2332947, 2011, A1,
[2] Patent: EP2661256, 2018, B1,
  • 11
  • [ 21739-92-4 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: CN108675976, 2018, A,
[2] Patent: CN108675976, 2018, A,
  • 12
  • [ 21900-52-7 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: CN108675976, 2018, A,
[2] Patent: CN108675976, 2018, A,
  • 13
  • [ 1103738-20-0 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: EP2332947, 2011, A1,
  • 14
  • [ 1352955-16-8 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: CN108675976, 2018, A,
  • 15
  • [ 461432-22-4 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: CN108675976, 2018, A,
  • 16
  • [ 108-21-4 ]
  • [ 1103738-30-2 ]
Reference: [1] Patent: CN108675976, 2018, A,
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