[ CAS No. 1344046-13-4 ]

Name: 1344046-13-4|3-Bromoquinoline-7-carboxylic acid|98%
Brand: Ambeed
SKU: A205498
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3d Animation Molecule Structure of 1344046-13-4

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Quality Control of [ 1344046-13-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1344046-13-4 ]

SDS Specification

Alternatived Products of [ 1344046-13-4 ]

Product Details of [ 1344046-13-4 ]

CAS No. :	1344046-13-4	MDL No. :	MFCD20327982
Formula :	C₁₀H₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VHZHOJLAAXVYSL-UHFFFAOYSA-N
M.W :	252.06	Pubchem ID :	71819690
Synonyms :

Calculated chemistry of [ 1344046-13-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.4
TPSA :	50.19 Å²

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) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.73
Log Po/w (XLOGP3) :	2.41
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	2.04
Log Po/w (SILICOS-IT) :	2.47
Consensus Log Po/w :	2.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-3.38
Solubility :	0.104 mg/ml ; 0.000413 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.197 mg/ml ; 0.000783 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.93
Solubility :	0.0295 mg/ml ; 0.000117 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.33

Safety of [ 1344046-13-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1344046-13-4 ]

* 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.

Downstream synthetic route of [ 1344046-13-4 ]

[ 1344046-13-4 ] Synthesis Path-Downstream 1~8

1
[ 1344046-13-4 ]
[ 2253094-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 60 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water; ethanol / 80 °C

Reference： [1]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - WO2018/218042, 2018, A1

2
[ 1344046-13-4 ]
[ 2253084-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 60 °C 2.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 110 °C

Reference： [1]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - WO2018/218042, 2018, A1

3
[ 1448427-99-3 ]
3-bromoquinoline-7-carboxylic acid [ No CAS ]
C₂₀H₁₇BrN₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	Stage #1: 3-bromoquinoline-7-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 6-[4-(propan-2-yl)-4H-1,2,4-triazol-3-yl]pyridin-2-amine In N,N-dimethyl-formamide at 60℃;	36 Example 36 HBTU (451 mg, 1.2 mmol, 1.2 eq) was added to a solution of 3-bromoquinoline-7- carboxylic acid (250 mg, 1.0 mmol, 1.0 eq) and Hunig’s base (0.87 mL, 5.0 mmol, 5.0 eq) in DMF (3.0 mL) and the reaction was stirred for 10 min at room temperature.6-(4-Isopropyl- 4H-1,2,4-triazol-3-yl)pyridin-2-amine (1-6) (222 mg, 1.1 mmol, 1.1 eq) was added and the resultant suspension was heated at 60 °C overnight. The reaction was partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with sat. NaHCO3, 10% citric acid, and brine. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The resultant brown gum was purified by column chromatography eluting with DCM/MeOH (0% MeOH , 8% MeOH) to afford pure compound 36 (82 mg, 0.19 mmol, 19%) as a brown amorphous solid: LCMS (ESI) m/z 437.06 (M+1).

Reference： [1]Current Patent Assignee: ENANTA PHARMACEUTICALS INC - WO2018/218042, 2018, A1 Location in patent: Page/Page column 79

4
[ 1344046-13-4 ]
[ 2415204-35-0 ]
[ 2415201-78-2 ]
[ 2415201-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere;	2.35 Method 35: Preparation of Compounds 120 and 121: 3-(4-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid and 3-(4-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid. 3-(4-((S)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid and 3-(4-((R)-6-((R)-tetrahydrofuran-2-carbonyl)-6-azaspiro[2.5]octan-1-yl)phenyl)quinoline-7-carboxylic acid A solution of ((R)-tetrahydrofuran-2-yl)(1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-6-azaspiro[2.5]octan-6-yl)methanone (450 mg, 1.10 mmol), 3-bromoquinoline-7-carboxylic acid (689 mg, 2.74 mmol), [1,1'-Bis(di phenylphosphino)ferrocene]dichloropalladium (89.3 mg, 0.11 mmol) and potassium phosphate (702 mg, 3.31 mmol) in 1,4-dioxane (15 mL) and water (3 mL) was stirred for 2 h at 80 °C under a nitrogen atmosphere. The mixture was cooled to room temperature and concentrated under reduced pressure. The crude product was purified by Prep-HPLC with water (0.1% FA) and ACN (40.0% up to 60.0% in 10 min). The product was separated by Chiral HPLC with the following conditions: Column: CHIRALPAK IF, 0.46 × 5 cm, 3 µm; mobile phase: hexanes (containing 0.1% formic acid): dichloromethane (3:1) and Methanol (hold 50% Methanol in 15 min); Detector: UV 254 nm to afford the first eluting peak as Compound 120 (119.2 mg, 24%) as a yellow solid and the second eluting peak as Compound 121 (119.3 mg , 34%) as a white solid. Compound 120: 1H NMR (400 MHz, DMSO-d6) δ (ppm): 13.30 (br, 1H), 9.39-9.38 (m, 1H), 8.74 (s, 1H), 8.60 (s, 1H), 8.15-8.08 (m, 2H), 7.86 (d, J=8.4 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H), 4.72-4.55 (m, 1H), 3.78-3.59 (m, 6H), 2.15-2.10 (m, 1H), 2.04-1.73 (m, 4H), 1.68-1.42 (m, 2H), 1.28-0.88 (m, 4H). LCMS (ES, m/z): 457 [M+H]+. Compound 121: 1H NMR (400 MHz, DMSO-d6) δ (ppm): 13.33 (br, 1H), 9.39 (s, 1H), 8.76 (s, 1H), 8.60 (s, 1H), 8.17-8.09 (m, 2H), 7.87 (d, J=8.0 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H), 4.70-4.58 (m, 1H), 3.78-3.61 (m, 4H), 3.27-3.18 (m, 2H), 2.16-1.71 (m, 5H), 1.68-1.47 (m, 2H), 1.28-0.90 (m, 4H). LCMS (ES, m/z): 457 [M+H]+.

Reference： [1]Current Patent Assignee: FORMA THERAPEUTICS HOLDINGS, INC - EP3636637, 2020, A1 Location in patent: Paragraph 0292-0296

5
[ 1344046-13-4 ]
[ 571150-08-8 ]
[ 2550442-79-8 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 3-bromoquinoline-7-carboxylic acid With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0℃; for 0.25h; Stage #2: N,N-diethyl 3-amino-6-chlorobenzenesulfonamide In ethyl acetate at 0 - 20℃; for 16h; Inert atmosphere;	1; II General Experimental Procedure II General procedure: T3P (35.0 equiv., 50% solution in EtOAc) was added to a stirred solution of the corresponding acid (1.0 equiv.) in pyridine (0.8 M) at 0 °C, and the reaction mixture was stirred for 15 minutes. Then, the corresponding aniline (1.0 equiv.) was added at 0 °C, and the reaction mixture was left to stir at rt for additional 16 hours under Nitrogen atmosphere. The progress of the reaction was monitored by thin layer chromatography and LC/MS. Upon completion of the reaction, the reaction mixture was filtered through a neutral alumina pad twice to remove the excess of T3P. The filtrate was concentrated in vacuo and the crude product was purified by prep- HPLC. After purification, the fractions containing the desired product were concentrated to a minimal volume, filtered through 0.4 ^m syringe filter and lyophilized to afford the product in > 95% purity.

Reference： [1]Current Patent Assignee: ANTIDOTE IP HOLDINGS LLC; ANTIDOTE IP HOLDINGS - WO2020/231739, 2020, A2 Location in patent: Paragraph 0189; 0242

6
[ 1344046-13-4 ]
[ 2550436-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: caesium carbonate; copper(l) iodide; N,N-dimethylglycine hydrochoride / 1,4-dioxane / 16 h / 90 °C / Sealed tube

Reference： [1]Current Patent Assignee: ANTIDOTE IP HOLDINGS LLC; ANTIDOTE IP HOLDINGS - WO2020/231739, 2020, A2

7
[ 1344046-13-4 ]
[ 2550438-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; HATU / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 110 °C / Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: ANTIDOTE IP HOLDINGS LLC; ANTIDOTE IP HOLDINGS - WO2020/231739, 2020, A2

8
[ 1344046-13-4 ]
[ 106877-33-2 ]
[ 2550438-32-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	1; I General Experimental Procedure I General procedure: Corresponding carboxylic acid (1.0 equiv) and corresponding aniline (1.1 equiv) were suspended in dry N,N-dimethyl formamide under argon atmosphere followed by the addition of triethylamine (1.2 equiv). Then HATU (1-[bis(dimethylamino) methylene]-1H-1,2,3- triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) (228 mg, 0.6 mmol, 1.2 equiv) was added, and the reaction mixture was stirred for 16 hours at rt. After dilution with water, the mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified on C18-silica gel (water/acetonitrile + 0.1% trifluoroacetic acid). The fractions containing the desired product were combined and treated with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the desired product in >95% purity as determined by HPLC.

Reference： [1]Current Patent Assignee: ANTIDOTE IP HOLDINGS LLC; ANTIDOTE IP HOLDINGS - WO2020/231739, 2020, A2 Location in patent: Paragraph 0188; 0223

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Ghs Precautionary Statements

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P321
P322
P330	Rinse mouth.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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.
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P401
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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. 1344046-13-4 ]

Quality Control of [ 1344046-13-4 ]

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Water Solubility

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[ 1344046-13-4 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 1344046-13-4 ]

Bromides

Carboxylic Acids

Related Parent Nucleus of [ 1344046-13-4 ]

Quinolines

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[ 1344046-13-4 ]

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[ 1344046-13-4 ]