[ CAS No. 519055-62-0 ] {[proInfo.proName]}

Name: 519055-62-0|N-((5-Bromothiophen-2-yl)sulfonyl)-2,4-dichlorobenzamide|98%
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SKU: A122315
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Quality Control of [ 519055-62-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 519055-62-0 ]

SDS Specification

Alternatived Products of [ 519055-62-0 ]

Product Details of [ 519055-62-0 ]

CAS No. :	519055-62-0	MDL No. :	N/A
Formula :	C₁₁H₆BrCl₂NO₃S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WWONFUQGBVOKOF-UHFFFAOYSA-N
M.W :	415.11	Pubchem ID :	10160238
Synonyms :	LY 573636	Chemical Name :	N-((5-Bromothiophen-2-yl)sulfonyl)-2,4-dichlorobenzamide

Calculated chemistry of [ 519055-62-0 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	82.84
TPSA :	99.86 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	4.62
Log Po/w (WLOGP) :	5.02
Log Po/w (MLOGP) :	2.78
Log Po/w (SILICOS-IT) :	4.05
Consensus Log Po/w :	3.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.47
Solubility :	0.00142 mg/ml ; 0.00000341 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.44
Solubility :	0.00015 mg/ml ; 0.000000361 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.1
Solubility :	0.000328 mg/ml ; 0.000000791 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.78

Safety of [ 519055-62-0 ]

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 [ 519055-62-0 ]

* 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 [ 519055-62-0 ]
Downstream synthetic route of [ 519055-62-0 ]

[ 519055-62-0 ] Synthesis Path-Upstream 1~6

1
[ 50-84-0 ]
[ 1152981-12-8 ]
[ 519055-62-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dicobalt octacarbonyl; tert-butylisonitrile In acetonitrile at 80℃; for 4 h;	0.5 mmol (0.0955 g) of 2,5-dichlorobenzoic acid, 0.75 mmol (0.2011 g) of 2-bromothiophenesulfonyl azide and 0.025 mmol (0.0086 g) of octacarbyldicobalt were weighed, respectively.Add to a 25 mL reaction tube;Then, 4 mL of acetonitrile solvent, 100 μl of t-butyl isocyanide measured by a micro syringe was sequentially added to the above reactor, and the whole reaction system was stirred at 80 ° C for 4 hours;After the completion of the reaction, the mixture was concentrated by rotary evaporation, and the mixture was applied and separated by column chromatography (column separation conditions: 200-300 mesh silica gel powder, mobile phase ethyl acetate: petroleum ether = 1:4, yielding 0.1583 g The object product was obtained as a white solid in a yield of 76percent.

Reference： [1] Chemistry--A European Journal, 2012, vol. 18, # 45, p. 14444 - 14453,10
[2] Chemistry - A European Journal, 2012, vol. 18, # 45, p. 14444 - 14453
[3] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9364 - 9369
[4] Patent: CN108558822, 2018, A, . Location in patent: Paragraph 0035; 0036; 0037; 0040; 0043

2
[ 53595-65-6 ]
[ 50-84-0 ]
[ 519055-62-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With dmap; 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 20℃; for 1 h;	DCM (2.0 mL) was added to a 20 mL vial containing DMAP (3.81 mg, 0.031 mmol), 2-chloro-1-methylpyridin-1-ium iodide (0.191 g, 0.748 mmol), 2,4-dichlorobenzoic acid (0.119 g, 0.623 mmol), 5-bromothiophene-2-sulfonamide (0.302 g, 1.25 mmol) at rt. After stirring for 5 min, TEA (0.261 ml, 1.869 mmol) was slowly added to the reaction mixture. The reaction was stirred at rt for 1 h. The reaction solvent was concentrated under vacuum and the crude residue was taken up in ethyl acetate, washed with 1N HCl (1 mL), water, and brine. The ethyl acetate layer was separated, dried (Na2SO4), filtered and concentrated. The crude material was purified by silica gel flash column chromatography eluting with ethyl acetate in hexane from 0 to 30percent to give the desired product (0.168 g, 65percent) as colorless crystals: ¹H NMR (499 MHz, CDCl3) δ 7.73 (d, J = 4.1 Hz, 1H), 7.71 (d, J = 8.5 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H), 7.36 (dd, J = 8.5, 1.9 Hz, 1H), 7.14 (d, J = 4.1 Hz, 1H).

Reference： [1] Tetrahedron Letters, 2019, vol. 60, # 3, p. 268 - 271

3
[ 53595-65-6 ]
[ 89-75-8 ]
[ 519055-62-0 ]

Reference： [1] Organic Process Research and Development, 2009, vol. 13, # 2, p. 255 - 262
[2] Organic Letters, 2018, vol. 20, # 19, p. 6302 - 6305

4
[ 53595-65-6 ]
[ 874-42-0 ]
[ 519055-62-0 ]

Reference： [1] Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6940 - 6945

5
[ 53595-65-6 ]
[ 50-84-0 ]
[ 519055-62-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 617 - 620

6
[ 50-84-0 ]
[ 519055-62-0 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 19, p. 6302 - 6305

[ 519055-62-0 ] Synthesis Path-Downstream 1~12

1
[ 53595-65-6 ]
[ 50-84-0 ]
[ 519055-62-0 ]

Yield	Reaction Conditions	Operation in experiment
59%		In a round-bottom flask under N2 were introduced respectively 2,4-dichlorobenzoic acid (270 mg, 1.4 mmol), anhydrous THF (30 mL),DMF (4 drops) and oxalyl chloride (470 L, 5.6 mmol). The reaction mixture was stirred overnight at room temperature and then concentrated under reduced pressure. In a round-bottom flask under N2 were introduced respectively 5-bromothiophene-2-sulfonamide (300mg, 1.2 mmol), EtOAc (10 mL), Et3N (300 L, 3.2 mmol) and DMAP (2mg, 0.02 mmol). A solution of 2,4-dichlorobenzoyl chloride, previously prepared in dried toluene (10 mL), was added via a syringe over 15min. The mixture was stirred for 5 h at 55 C under N2, cooled to room temperature and quenched with 0.5 M aqueous HCl solution (40 mL).The resulting mixture was extracted with EtOAc (3 × 600 mL). The combined organic layers were dried over anhydrous MgSO4, filteredand concentrated under reduced pressure. The crude residue was purifiedby silica gel chromatography using DCM as eluent to afford 1k.Yield: 300 mg (59%); yellow solid; mp 114-116 C.1H NMR (400 MHz, CDCl3): = 9.07 (br s, 1 H), 7.74 (d, J = 6.0 Hz, 1 H),7.73 (d, J = 1.6 Hz, 1 H), 7.45 (d, J = 1.9 Hz, 1 H), 7.36 (dd, J = 8.4, 2.0 Hz,1 H), 7.13 (d, J = 4.1 Hz, 1 H).13C NMR (100 MHz, CDCl3): = 162.2, 139.5, 138.6, 136.0, 132.5,131.9, 130.7, 130.5, 129.3, 128.2, 123.3.

Reference： [1]Synthesis,2019,vol. 51,p. 4393 - 4400
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 617 - 620

2
[ 53595-65-6 ]
[ 89-75-8 ]
[ 519055-62-0 ]

Reference： [1]Organic Process Research and Development,2009,vol. 13,p. 255 - 262
[2]Organic Letters,2018,vol. 20,p. 6302 - 6305

3
[ 53595-65-6 ]
[ 519055-62-0 ]
[ 1114547-80-6 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: 2,4-dichloro-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at -45 - 4℃; for 2h; Stage #2: 5-bromo-thiophene-2-sulfonamide In dichloromethane at -40 - 20℃;

Reference： [1]Yates, Matthew H.; Kallman, Neil J.; Ley, Christopher P.; Wei, Jeffrey N. [Organic Process Research and Development, 2009, vol. 13, # 2, p. 255 - 262]

4
[ 519055-62-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
87.2%	With sodium hydroxide In water; isopropyl alcohol at 25℃; Inert atmosphere; Large scale reaction;

Reference： [1]Location in patent: experimental part Yates, Matthew H.; Kallman, Neil J.; Ley, Christopher P.; Wei, Jeffrey N. [Organic Process Research and Development, 2009, vol. 13, # 2, p. 255 - 262]

5
[ 50-84-0 ]
[ 1152981-12-8 ]
[ 519055-62-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane; triethylamine In chlorobenzene at 20 - 130℃; for 12h; chemoselective reaction;
76%	With dicobalt octacarbonyl; tert-butylisonitrile In acetonitrile at 80℃; for 4h;
76%	With dicobalt octacarbonyl; tert-butylisonitrile In acetonitrile at 80℃; for 4h;	1 The method for synthesizing N-((5-bromothien-2-yl)sulfonyl)-2,4-dichlorobenzamide of the present embodiment comprises the following steps 0.5 mmol (0.0955 g) of 2,5-dichlorobenzoic acid, 0.75 mmol (0.2011 g) of 2-bromothiophenesulfonyl azide and 0.025 mmol (0.0086 g) of octacarbyldicobalt were weighed, respectively.Add to a 25 mL reaction tube;Then, 4 mL of acetonitrile solvent, 100 μl of t-butyl isocyanide measured by a micro syringe was sequentially added to the above reactor, and the whole reaction system was stirred at 80 ° C for 4 hours;After the completion of the reaction, the mixture was concentrated by rotary evaporation, and the mixture was applied and separated by column chromatography (column separation conditions: 200-300 mesh silica gel powder, mobile phase ethyl acetate: petroleum ether = 1:4, yielding 0.1583 g The object product was obtained as a white solid in a yield of 76%.

Reference： [1]Kosal, Andrew D.; Wilson, Erin E.; Ashfeld, Brandon L. [Chemistry - A European Journal, 2012, vol. 18, # 45, p. 14444 - 14453,10]
[2]Fang, Yue; Gu, Zheng-Yang; Wang, Shun-Yi; Yang, Jin-Ming; Ji, Shun-Jun [Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9364 - 9369]
[3]Current Patent Assignee: JINMING PHARMACEUTICAL; YANCHENG TEACHERS UNIVERSITY - CN108558822, 2018, A Location in patent: Paragraph 0035; 0036; 0037; 0040; 0043

6
[ 53595-65-6 ]
[ 874-42-0 ]
[ 519055-62-0 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6940 - 6945

7
[ 519055-62-0 ]
[ 2246440-34-4 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: 2,4-dichloro-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide With palladium diacetate In methanol at 20℃; for 24h; Stage #2: With C₄H₄⁽¹²⁵⁾INO₂; acetic acid In methanol at 20℃; for 0.5h;	2,4-Dichloro-6-iodo-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide(2k)12 To a round-bottom flask were introduced respectively 1k (100 mg,0.24 mmol), MeOH (5 mL) and Pd(OAc)2 (60 mg, 0.26 mmol). The reaction mixture was stirred for 24 h at room temperature and then acetic acid (14 L, 0.24 mmol), NIS (54 mg, 0.24 mmol) and MeOH (1mL) were added. The reaction mixture was stirred for 30 min at room temperature and the resulting mixture was diluted with H2O (2 mL),quenched with saturated aqueous Na2S2O3 solution (4 mL) and extractedwith EtOAc (3 × 6 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by reverse-phase gel chromatography using HCOOH/H2O/CH3CN as eluent (0.1:95:5 to0.1:5:95) to afford 2k.Yield: 62 mg (47%); brown powder; mp 70-72 °C.1H NMR (400 MHz, CDCl3): = 8.88 (br s, 1 H), 7.74 (d, J = 4.0 Hz, 1 H),7.68 (d, J = 1.8 Hz, 1 H), 7.36 (d, J = 1.8 Hz, 1 H), 7.15 (d, J = 4.0 Hz, 1 H).13C NMR (100 MHz, CDCl3): = 163.3, 137.9, 137.4, 137.4, 137.1,136.3, 131.7, 130.7, 129.5, 123.3, 92.0.
	Stage #1: 2,4-dichloro-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide With palladium diacetate In methanol at 20℃; for 24h; Stage #2: With C₄H₄⁽¹²⁵⁾INO₂; trifluoroacetic acid In methanol at 20℃; for 0.25h;

Reference： [1]Babin, Victor; Benoist, Florian; Bouillon, Jean-Philippe; Cailly, Thomas; Dubost, Emmanuelle; Fabis, Frédéric; Hébert, Alexandra; Pigrée, Gilbert [Synthesis, 2019, vol. 51, # 23, p. 4393 - 4400]
[2]Dubost, Emmanuelle; Babin, Victor; Benoist, Florian; Hébert, Alexandra; Barbey, Pierre; Chollet, Céline; Bouillon, Jean-Philippe; Manrique, Alain; Pieters, Grégory; Fabis, Frédéric; Cailly, Thomas [Organic Letters, 2018, vol. 20, # 19, p. 6302 - 6305]

8
[ 519055-62-0 ]
[ 2246440-19-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: 2,4-dichloro-N-[(5-bromo-2-thienyl)sulfonyl]benzenecarboxamide With palladium diacetate In methanol at 20℃; for 24h; Stage #2: With N-iodo-succinimide; acetic acid In methanol at 20℃; for 0.5h;

Reference： [1]Dubost, Emmanuelle; Babin, Victor; Benoist, Florian; Hébert, Alexandra; Barbey, Pierre; Chollet, Céline; Bouillon, Jean-Philippe; Manrique, Alain; Pieters, Grégory; Fabis, Frédéric; Cailly, Thomas [Organic Letters, 2018, vol. 20, # 19, p. 6302 - 6305]

9
[ 50-84-0 ]
[ 519055-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / tetrahydrofuran / 20 °C / Inert atmosphere 2: triethylamine; dmap / ethyl acetate; toluene / 5 h / 55 °C / Inert atmosphere

10
[ 53595-65-6 ]
[ 50-84-0 ]
C₁₀H₉BrN₂O₂S₂ [ No CAS ]
[ 519055-62-0 ]

Yield	Reaction Conditions	Operation in experiment
15%; 65%	With dmap; 2-chloro-1-methyl-pyridinium iodide; triethylamine; In dichloromethane; at 20℃; for 1h;	DCM (2.0 mL) was added to a 20 mL vial containing DMAP (3.81 mg, 0.031 mmol), 2-chloro-1-methylpyridin-1-ium iodide (0.191 g, 0.748 mmol), 2,4-dichlorobenzoic acid (0.119 g, 0.623 mmol), 5-bromothiophene-2-sulfonamide (0.302 g, 1.25 mmol) at rt. After stirring for 5 min, TEA (0.261 ml, 1.869 mmol) was slowly added to the reaction mixture. The reaction was stirred at rt for 1 h. The reaction solvent was concentrated under vacuum and the crude residue was taken up in ethyl acetate, washed with 1N HCl (1 mL), water, and brine. The ethyl acetate layer was separated, dried (Na2SO4), filtered and concentrated. The crude material was purified by silica gel flash column chromatography eluting with ethyl acetate in hexane from 0 to 30% to give the desired product (0.168 g, 65%) as colorless crystals: 1H NMR (499 MHz, CDCl3) δ 7.73 (d, J = 4.1 Hz, 1H), 7.71 (d, J = 8.5 Hz, 1H), 7.45 (d, J = 1.9 Hz, 1H), 7.36 (dd, J = 8.5, 1.9 Hz, 1H), 7.14 (d, J = 4.1 Hz, 1H).

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 268 - 271

11
[ 6773-29-1 ]
[ 519055-62-0 ]
[ 2740621-29-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In methanol at 25℃; for 1.5h; Green chemistry;

Reference： [1]Dong, Yi; Mei, Bo; Zhang, Xue-Peng; Xu, Heng [Journal of Organic Chemistry, 2021, vol. 86, # 17, p. 11660 - 11672]

12
[ 73789-56-7 ]
[ 150884-50-7 ]
[ 519055-62-0 ]
[ 2730096-75-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethyl acetate; toluene at 22℃; for 16h; Sealed tube; Inert atmosphere;

Reference： [1]Matheau-Raven, Daniel; Boulter, Elizabeth; Rogova, Tatiana; Dixon, Darren J. [Organic Letters, 2021, vol. 23, # 21, p. 8209 - 8213]

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[ 519055-62-0 ]

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[ 50-84-0 ]

2,4-Dichlorobenzoic acid

Similar Product of
[ 519055-62-0 ]

A414391[ 519055-63-1 ]

Sodium ((5-bromothiophen-2-yl)sulfonyl)(2,4-dichlorobenzoyl)amide

Reason: Free-salt

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Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 519055-62-0 ] {[proInfo.proName]}

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[ 519055-62-0 ] Synthesis Path-Upstream 1~6

[ 519055-62-0 ] Synthesis Path-Downstream 1~12

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[ 519055-62-0 ]

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