[ CAS No. 104-86-9 ] {[proInfo.proName]}

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Quality Control of [ 104-86-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 104-86-9 ]

SDS Specification

Alternatived Products of [ 104-86-9 ]

Product Citations Expand+

Quinolone analogues of benzothiazinone: Synthesis, antitubercular structure-activity relationship and ADME profiling

Dube, Phelelisiwe S. ; Legoabe, Lesetja J. ; Jordaan, Audrey , et al. Eur. J. Med. Chem.,2023,258,115539. DOI: 10.1016/j.ejmech.2023.115539 PubMed ID: 37321107

Abstract: Mycobacterium tuberculosis (Mtb) has an impermeable cell wall which gives it an inherent ability to resist many antibiotics. DprE1, an essential enzyme in Mtb cell wall synthesis, has been validated as a target for several TB drug candidates. The most potent and developmentally advanced DprE1 inhibitor, PBTZ169, is still undergoing clin. development. With high attrition rate, there is need to populate the development pipeline. Using a scaffold hopping strategy, we imprinted the benzenoid ring of PBTZ169 onto a quinolone nucleus. Twenty-two compounds were synthesized and screened for activity against Mtb, with six compounds exhibiting sub micromolar activity of MIC90 <0.244 μM. Compound 25 further demonstrated sub-micromolar activity when evaluated against wild-type and fluoroquinolone-resistant Mtb strains. This compound maintained its sub-micromolar activity against a DprE1 P116S mutant strain but showed a significant reduction in activity when tested against the DprE1 C387S mutant.

Keywords: DprE1 ; Quinolone ; Nitro compounds ; Mycobacterium tuberculosis ; Benzothiazinone

Purchased from AmBeed: 104-86-9 ; 100-82-3 ; 4152-90-3 ; 1377239-83-2 ; 100-81-2 ; 400-98-6 ; 72235-53-1 ; 89-97-4 ; 190140-20-6

Product Details of [ 104-86-9 ]

CAS No. :	104-86-9	MDL No. :	MFCD00008121
Formula :	C₇H₈ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YMVFJGSXZNNUDW-UHFFFAOYSA-N
M.W :	141.60	Pubchem ID :	66036
Synonyms :		Chemical Name :	(4-Chlorophenyl)methanamine

Calculated chemistry of [ 104-86-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.13
TPSA :	26.02 ?2

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) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	1.65
Log Po/w (WLOGP) :	1.65
Log Po/w (MLOGP) :	2.14
Log Po/w (SILICOS-IT) :	2.1
Consensus Log Po/w :	1.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.18
Solubility :	0.925 mg/ml ; 0.00654 mol/l
Class :	Soluble
Log S (Ali) :	-1.81
Solubility :	2.19 mg/ml ; 0.0155 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.03
Solubility :	0.131 mg/ml ; 0.000927 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 104-86-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P210-P273-P280-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H227-H302+H312-H314-H402	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 104-86-9 ]

* 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 [ 104-86-9 ]
Downstream synthetic route of [ 104-86-9 ]

[ 104-86-9 ] Synthesis Path-Upstream 1~2

1
[ 104-86-9 ]
[ 14123-76-3 ]

Reference： [1] Patent: WO2016/83816, 2016, A1,

2
[ 6342-56-9 ]
[ 104-86-9 ]
[ 14123-76-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 17, p. 7412 - 7424

[ 104-86-9 ] Synthesis Path-Downstream 1~12

1
[ 3512-75-2 ]
[ 104-86-9 ]
(4-chloro-benzyl)-(2,6-dimethyl-[4]pyridyl)-amine [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1953,vol. 73,p. 145,146,147
Chem.Abstr.,1953,p. 11 192

2
N,N-bis(p-chlorobenzylamino)ethane dihydrobromide [ No CAS ]
[ 33537-99-4 ]
[ 104-86-9 ]

Reference： [1]Synthetic Communications,1997,vol. 27,p. 2533 - 2538

3
[ 931-53-3 ]
[ 4214-79-3 ]
[ 123-38-6 ]
[ 104-86-9 ]
2-(N-(4-chlorobenzyl)-N-(5-chloropyridin-2-yl)amino)-N-cyclohexylbutanamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4169 - 4180

4
[ 132898-96-5 ]
[ 104-86-9 ]
[ 953029-02-2 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 4948 - 4956

5
[ 149057-19-2 ]
[ 104-86-9 ]
[ 1311150-48-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3142 - 3147

6
[ 104-86-9 ]
[ 1379686-30-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4413 - 4417

7
[ 97-08-5 ]
[ 104-86-9 ]
4-chloro-3-nitro-N-4-chlorobenzylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 20℃;	General procedure: <strong>[97-08-5]4-Chloro-3-nitrobenzenesulfonyl chloride</strong> (1 equiv.) anddifferent amines (2 equiv.) were added to a 50 mL roundbottomedflask and dissolved in acetonitrile (25 mL). Thecontents were then stirred for 1-2 h at room temperature.Afterward, the solvent was removed under vacuum andthe product was washed with a dilute solution (5 %) ofNaHCO3 and filtered.

Reference： [1]Amino Acids,2016,vol. 48,p. 445 - 459

8
[ 104-86-9 ]
[ 1180-71-8 ]
N-(4-chlorobenzyl)-2-((1S,3aS,4aR,4bR,9aR,11aS)-1-(furan-3-yl)-9a-(hydroxymethyl)-4b,7,7,11a-tetramethyl-3,5-dioxotetradecahydroisobenzofuro[5,4-f]oxireno[2,3-d]isochromen-9-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With montmorillonite K-10; In ethanol; at 80℃; for 0.5h;Sealed tube; Microwave irradiation;	General procedure: To a solution of 1 (2.0 mmol) in absolute EtOH (8.0 mL)in a glass tube was added dropwise the appropriate amine(3.6 mmol) and K-10 (0.3 g mmol-1); the quartz tubewas sealed with reaction mixture and introduced intoa microwave oven. The flask was irradiated for 30 min(150 W) the temperature of 80 C. After completion of thereaction the mixture was filtered, the organic phase wasdried with Na2SO4, filtered and the solvent was evaporatedunder reduced pressure to give the crude products. All thecompounds were purified by column chromatographyon silica gel using 2-5% EtOH-CH2Cl2 as eluent to giveanalytically pure products 3a-m. The products werecharacterized by corresponding spectroscopic data (1H and13C NMR, and HRMS).

Reference： [1]Journal of the Brazilian Chemical Society,2016,vol. 27,p. 161 - 178

9
[ 57772-50-6 ]
[ 104-86-9 ]
8-methyl-2-(4-chlorophenyl)quinazoline [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5781 - 5789

10
[ 5926-51-2 ]
[ 104-86-9 ]
N-4-chlorobenzyl-2-bromomaleimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.3%		Bromo maleic anhydride 0.6mmol weighed into three neck round bottom flask, 10ml of acetone was dissolved, 4-chloro-benzylamine 0.5mmol dissolved by acetone 10ml was slowly dropped into a constant pressure funnel three-neck flask with magnetic stirring reaction at room temperature for IH, the acetone solvent was removed by rotary evaporation, 15ml of toluene as a solvent instead, 0.02g of anhydrous sodium acetate were added to the reaction system, 0.2ml of triethylamine, 0.05 g of hydroquinone was slowly warmed to 115 reflux 2.5h, the reaction is tracked by thin layer chromatography on silica gel.After the reaction was cooled to room temperature, the solvent was removed by rotary evaporation, to obtain a concentrate, the concentrate was subjected to silica gel column chromatography (eluent: VPetroleum ether: VEthyl acetate= 12: 1), and collecting the target fluid, the rotation solvent in vacuo to give the desired product.Yield 53.3.

Reference： [1]Patent: CN107162950,2017,A .Location in patent: Paragraph 0039-0041

11
[ 437-86-5 ]
[ 104-86-9 ]
C₁₄H₁₃ClN₂O₂ [ No CAS ]

Reference： [1]Patent: WO2019/28308,2019,A1 .Location in patent: Page/Page column 48; 52

12
[ 32608-29-0 ]
[ 104-86-9 ]
2-(4-chlorobenzylamino)-4-chloro-8-methoxyquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In tetrahydrofuran; for 16h;Inert atmosphere; Reflux;	To a solution under nitrogen gas of <strong>[32608-29-0]2,4-dichloro-8-methoxyquinoline</strong> 6-1 (2.0 g, 8.81 mmol) in dry THF (20 ml) was added 4-chlorobenzylamine (1.86 g, 13.21 mmol) and K2CO3 (2.43 g, 17.6 mmol). The resulting mixture was degassed 5 min with nitrogen, then Xantphos (509 mg, 0.81 mmol) and Pd(OAc)2 (98 mg, 0.44 mmol) were added and the reaction mixture was heated under reflux for 16 hours. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between brine and EtOAC and the aqueous layer was extracted with EtOAC. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a light brown solid. The crude product was purified by flash chromatography (gradient petroleum ether/EtOAC from 09/01 to 04/06) to give 1.2 g (yield 41%) of a brown solid corresponding to 2-(4-chlorobenzylamino)-4-chloro-8-methoxyquinoline (6-2). HPLC-MS, Method D: tr = 1.30 min, (ES+) C17H14Cl2N2O required 332; found 333 [M+H] 1H NMR (400 MHz, CDCl3)

Reference： [1]Patent: EP3620164,2020,A1 .Location in patent: Paragraph 1461; 1462

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

Historical Records

Related Functional Groups of
[ 104-86-9 ]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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.
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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
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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
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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. 104-86-9 ] {[proInfo.proName]}

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