[ CAS No. 123-08-0 ] {[proInfo.proName]}

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2D 3D

Structure of 123-08-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 123-08-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 123-08-0 ]

SDS Specification

Alternatived Products of [ 123-08-0 ]

Product Citations Expand+

Nitrothiazole-Thiazolidinone Hybrids: Synthesis and in Vitro Antimicrobial Evaluation

Dylan Hart ; Lesetja J. Legoabe ; Omobolanle J. Jesumoroti , et al. Chem. Biodivers.,2022,19(11):e202200729. DOI: 10.1002/cbdv.202200729 PubMed ID: 36102043

Abstract: Herein we report the synthesis

Purchased from AmBeed: class="">613-45-6 ; class="">121-66-4 ; class="">587-04-2 ; class="">104-87-0 ; class="">552-89-6 ; class="">456-48-4 ; class="">830-79-5 ; class="">555-16-8 ; class="">104-88-1 ; class="">591-31-1 ; class="">3132-99-8 ; class="">446-52-6 ; class="">459-57-4 ; class="">529-20-4 ; class="">6287-38-3 ; class="">123-08-0 ; class="span_more span_less">100-52-7 ; class="span_more span_less">349121-09-1 ; class="span_more span_less">89-98-5 class="keywords_more email-color more_span" onclick="change_span_more(this)">...More

Design, synthesis and evaluation of amino-3, 5-dicyanopyryridines and thieno [2, 3-b] pyridines as ligands of adenosine receptors

Nkomba, Gaofenngwe ; Terre' ; Blanche, Gisella , et al. Research Square,2022. DOI: 10.21203/rs.3.rs-1500396/v1 PubMed ID: 35634433

Abstract: Due to the implication of adenosine in seizure suppression, adenosine-based therapies such as adenosine receptor (AR) agonists have been investigated. This study aimed at investigating thieno[2,3 b]pyridine derivatives as non-nucleoside A1 agonists that could be used in pharmaco-resistant epilepsy (PRE). Compound 7c (thieno[2,3-b]pyridine derivative), displayed good binding a nity to the rA1 AR (Ki = 61.9 nM). This could be a breakthrough for further investigation of this heterocyclic scaffold as potential ligand. In silico evaluation of this compound raised bioavailability concerns but performed well on drug likeness tests. The effect of intramolecular cyclisation that occurs during synthesis of thieno[2,3 b]pyridines from the lead compounds, amino-3,5-dicyanopyridine derivatives ( 6a-s) in relation to AR binding was also evaluated. A signi cant loss of activity against rA1/rA2A ARs with cyclisation was revealed. Amino-3,5-dicyanopyridines exhibited greater a nity towards rA1 ARs (Ki

Keywords: Amino-3,5-dicyanopyryridines ; Thieno[2,3-b]pyridines ; Intramolecular cyclisation ; Adenosine A1/A2A receptors ; Epilepsy

Purchased from AmBeed: 123-08-0 ; 68470-59-7 ; 6515-58-8

Product Details of [ 123-08-0 ]

CAS No. :	123-08-0	MDL No. :	MFCD00006939
Formula :	C₇H₆O₂	Boiling Point :	-
Linear Structure Formula :	C₆H₄(OH)CHO	InChI Key :	RGHHSNMVTDWUBI-UHFFFAOYSA-N
M.W :	122.12	Pubchem ID :	126
Synonyms :	4-Formylphenol;p-Formylphenol;4-Hydroxybenzaldehyde	Chemical Name :	4-Hydroxybenzaldehyde

Calculated chemistry of [ 123-08-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.85
TPSA :	37.3 ?2

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) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.99
Log Po/w (XLOGP3) :	1.35
Log Po/w (WLOGP) :	1.2
Log Po/w (MLOGP) :	0.79
Log Po/w (SILICOS-IT) :	1.52
Consensus Log Po/w :	1.17

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.87
Solubility :	1.63 mg/ml ; 0.0133 mol/l
Class :	Very soluble
Log S (Ali) :	-1.74
Solubility :	2.25 mg/ml ; 0.0184 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.72
Solubility :	2.31 mg/ml ; 0.0189 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 123-08-0 ]

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 [ 123-08-0 ]

* 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 [ 123-08-0 ]
Downstream synthetic route of [ 123-08-0 ]

[ 123-08-0 ] Synthesis Path-Upstream 1~1

1
[ 76-83-5 ]
[ 123-08-0 ]
[ 892112-24-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6 h;	General procedure: The 4-hydroxybenzaldehyde 4 (0.8 g, 6.5 mmol) was reacted with 4-monometoxytriphenylmethyl (1.0 g, 3.2 mmol) in 10 mL of anhydrous DCM in the presence of DIEA (2.2 mL, 12.9 mmol). After 6 h at r.t., the reaction was quenched by dilution with DCM (100 mL), and the organic phase was washed three times with a solution of 0.1 M NaOH (3×100 mL). The organic phase was dried with MgSO₄, and then the solvent was removed under vacuum. The crude material was then purified on a column of silica gel (70 g) suspended in hexane/EtOAc 70:30 (v/v) with 1percent of TEA, leading to product 5 (1.05 g, 82percent). ¹H NMR (400 MHz, 25°C, δ, ppm in CDCl₃): δ 9.76 (s, 1H), 7.57–7.25 (complex signals, 14H), 6.86 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 3.77 (s, 3H). ¹³C NMR (100 MHz, 25°C, δ, ppm in CDCl₃): δ 190.7, 161.9, 158.7, 143.8, 134.9, 130.6, 130.2, 128.3, 127.8, 127.3, 120.3, 113.1, 91.1, 55.0. Product 5 (1.05 g, 2.66 mmol) was subsequently treated with 0.25 g of NaBH₄ (6.60 mmol) in THF (10 mL) for 6 h at r.t. The mixture was diluted with DCM (3×100 mL), and the organic phase was washed three times with water (100 mL). The organic phase was dried with MgSO₄, and then the solvent was removed under vacuum. The crude solid thus obtained was purified on a column of silica gel (70 g) suspended in hexane/EtOAc 60:40 (v/v) with 1percent of TEA. From the column was recovered 0.845 g of clean desired product 6 (2.13 mmol, 80percent). ¹H NMR (400 MHz, 25°C, δ, ppm in CDCl₃): δ 7.49 (d, J=6.0 Hz, 4H), 7.37–7.22 (complex signals, 8H), 6.98 (d, J=7.2 Hz, 2H), 6.79 (d, J=7.2 Hz, 2H), 6.70 (d, J=6.8 Hz, 2H), 4.45 (s, 2H), 3.75 (s, 3H). ¹³C NMR (100 MHz, 25°C, δ, ppm in CDCl₃): δ 158.4, 155.8, 144.5, 135.6, 133.3, 130.4, 128.6, 127.6, 127.4, 126.9, 120.6, 112.8, 90.0, 64.8, 55.0. Then, 0.40 g (1.01 mmol) of product 6 was reacted with N,N-diisopropyldichlorophosphoramidite (124 μL, 0.67 mmol) in the presence of DIEA (348 μL, 2.68 mmol) in DCM (7 mL). After 1.5 h, the reaction was quenched by dilution with DCM, and the organic phase was washed three times with cold water. The organic phase was dried with MgSO₄ and the solvent removed under vacuum. The material was purified with column chromatography of silica gel in hexane/EtOAc 85:15 (v/v) with 2percent of TEA. From the column was recovered 0.74 g of clean desired product (1, 87percent).

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 10, p. 2979 - 2988
[2] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1227 - 1229

[ 123-08-0 ] Synthesis Path-Downstream 1~10

1
[ 123-08-0 ]
[ 2314-36-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sulfuryl dichloride; In chloroform;Inert atmosphere; Reflux;	Compound R53 (4.9 g, 40 mmol) was dissolved in 80 ml of dry chloroform, followed by argon gasProtected, heated to reflux, slowly added dropwise a solution of 20 ml of sulfonyl chloride (6.4 ml, 80 mmol) in chloroform, and then refluxed overnight. The reaction solution was spin-dried and purified on a silica gel column. Yield 4.2g (55percent).

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2936 - 2941
[2]Patent: CN104341347,2018,B .Location in patent: Paragraph 0134; 0135
[3]Chemische Berichte,1904,vol. 37,p. 4033
[4]Chemische Berichte,1896,vol. 29,p. 2357

2
[ 123-08-0 ]
/PXGAB₁₁₄--212/ [ No CAS ]
[ 61439-59-6 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 1223 - 1227

3
[ 13220-33-2 ]
[ 123-08-0 ]
C₁₂H₁₅NO₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6467 - 6471

4
[ 558-42-9 ]
[ 123-08-0 ]
[ 1107662-91-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux;	Example 2A4-(2-Hydroxy-2-methylpropoxy)benzaldehyde5.00 g (40.94 mmol) of 4-hydroxybenzaldehyde, 4.44 g (40.94 mmol) of 1-chloro-2-methyl-2-propanol and 6.08 g (57.32 mmol) of sodium carbonate are initially charged in 50 ml of dry DMF and stirred under reflux for 24 h.After cooling to RT, 20 ml of ethyl acetate and 20 ml of sat. aqueous sodium bicarbonate solution are added.The phases are separated, and the organic phase is dried over magnesium sulfate.After removal of the solvent, the residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 5:1?1:1).This gives a reddish solid which is used without further purification for the subsequent step.Yield: 4.40 g (50percent of theory, 90percent purity)LC-MS (method 2): Rt=1.37 min; MS (ESIpos): m/z=195 [M+H]+.
	With sodium carbonate; In N,N-dimethyl-formamide; at 130℃;	5 g (40.94 mmol) of 4-hydroxybenzaldehyde were initially charged in 50 ml of DMF. 4.45 g (40.94 mmol) of 1-chloro-2-methylpropan-2-ol and 6.08 g (57.32 mmol) of sodium carbonate were added, and the mixture was then stirred at 130° C. overnight. Saturated aqueous sodium bicarbonate solution/ethyl acetate were added to the reaction mixture. The precipitate was filtered off and discarded. The two phases were separated from one another, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated using a rotary evaporator. The residue was purified by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 5/1?1/2). Yield: 8.6 g (82percent of theory, 76percent pure) LC-MS (Method 4): Rt=1.17 min; MS (ESIpos): m/z=195 [M+H]+. 1H NMR (400 MHz, DMSO-d6): delta=9.87 (s, 1H), 7.86 (d, 2H), 7.12 (d, 2H), 4.70 (s, 1H), 3.84 (s, 2H), 1.21 (s, 6H).

Reference： [1]Patent: US2011/130377,2011,A1 .Location in patent: Page/Page column 19
[2]Patent: US2013/210795,2013,A1 .Location in patent: Paragraph 0402-0406

5
[ 4876-10-2 ]
[ 123-08-0 ]
[ 1041095-99-1 ]

Reference： [1]Monatshefte fur Chemie,2012,vol. 143,p. 1075 - 1086

6
[ 57497-39-9 ]
[ 123-08-0 ]
[ 93376-44-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium hydrogencarbonate; In ethanol; at 100℃; for 0.166667h;Microwave irradiation;	General procedure: A mixture of the corresponding hydroxy benzaldehyde (1 equiv), N-tert-buthyl hydroxylamine hydrochloride (1.1 equiv), and sodium bicarbonate (1.1 equiv) in absolute ethanol (5 mL/mmol) as solvent was heated under microwave irradiation until the carbonyl compound was not present or there was no progress in the reaction (checked by TLC). The solvent was removed in vacuo and the reaction mixture diluted with H2O and extracted with EtOAc. After the workup of the combined organic layers, the residue was purified by column chromatography (SiO2, mixtures of petroleum ether/EtOAc).

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 58,p. 44 - 49

7
[ 36062-04-1 ]
[ 123-08-0 ]
[ 57-13-6 ]
[ 1432038-15-7 ]

Yield	Reaction Conditions	Operation in experiment
37%		General procedure: To a solution of the corresponding aromatic aldehyde (0.27 mmol) in EtOH (0.5 mL) was added urea (0.54 mmol) and CuSO4·5H2O (0.054 mmol). The mixture was stirred at 80 °C for 15 minutes before tetrahydrocurcumin or tetrahydrodemethoxycurcumin (0.27 mmol) was added. The reaction mixture was continued stirring for 24 hours and quenched with water (2 mL). The solution was washed with water (10 mL) and extracted with EtOAc (415 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford crude product as a yellow brown oil. Purification was accomplished by column chromatography eluting with 60percent-75percent EtOAc/hexane to furnish compounds 8-17.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2880 - 2882

8
[ 78364-55-3 ]
[ 123-08-0 ]
C₁₄H₁₀FN₃OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 70 - 80℃; for 3h;	General procedure: The mixture of <strong>[78364-55-3]6-fluoro-2-hydrazinylbenzo[d]thiazole</strong> (2) (0.01 mol) and benzalde-hyde/substituted benzaldehyde (0.01 mol) was reuxed in ethanol (15 ml) at 70?80 °C for 3 h. The separated product obtained was ltered off, washed withdistilled water and recrystallized from methanol to give the correspondinghydrazone. The product obtained was further dissolved in acetic acid (20 ml) atroom temperature followed by the addition of sodium acetate (0.5 g). Bromine(2 mmol) in acetic acid (10 ml) was added dropwise to the reuxing reactionmixture. After 1 h, the mixture was poured onto crushed ice (100 g). The precipitateobtained was ltered off and crystallized from ethanol-dimethylformamide (1:1) togive crystals of (3a?3t).

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 8329 - 8344

9
[ 7474-78-4 ]
[ 123-08-0 ]
2-(4-hydroxyphenyl)-1H-benzimidazole-5-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium metabisulfite; In ethanol; water; for 24h;Reflux;	General procedure: To a solution of the appropriate 3,4-diaminobenzene derivative (1ad)(2 mmol) in ethanol (15 mL) 2.85 N aqueous solution of sodium metabisulphite (1.6 mL) and the appropriate substituted arylaldehyde(2 mmol) were added. The reaction mixture was heated at reflux for 24 h. The solvent was then evaporated under reduced pressure. The residue was added with HCl 1 N (10 mL), the formed precipitate was filtered off, washed with water (3×10 mL) and purified by crystallization from the adequate solvent to give the title compounds.Following the general procedure benzimidazoles 3 [19], 4 [20], 5 [21],7 [24], 6, 32 and 33 [15] were prepared and their analytical and spectral data are in agreement with those reported in literature.

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2017,vol. 32,p. 527 - 537
[2]Bioorganic Chemistry,2019

10
[ 123-08-0 ]
[ 61439-59-6 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 12002 - 12005

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Technical Information

? Acidity of Phenols ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Chan-Lam Coupling Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Fischer Indole Synthesis ? Grignard Reaction ? Halogenation of Phenols ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Phenols ? Passerini Reaction ? Paternò-Büchi Reaction ? Pechmann Coumarin Synthesis ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Reimer-Tiemann Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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

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[ CAS No. 123-08-0 ] {[proInfo.proName]}

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[ 123-08-0 ] Synthesis Path-Upstream 1~1

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