[ CAS No. 4518-10-9 ] {[proInfo.proName]}

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Quality Control of [ 4518-10-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4518-10-9 ]

SDS Specification

Alternatived Products of [ 4518-10-9 ]

Product Details of [ 4518-10-9 ]

CAS No. :	4518-10-9	MDL No. :	MFCD00017102
Formula :	C₈H₉NO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	VZDNXXPBYLGWOS-UHFFFAOYSA-N
M.W :	151.16	Pubchem ID :	78274
Synonyms :

Calculated chemistry of [ 4518-10-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.13
TPSA :	52.32 ?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) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	1.54
Log Po/w (WLOGP) :	1.06
Log Po/w (MLOGP) :	1.32
Log Po/w (SILICOS-IT) :	0.97
Consensus Log Po/w :	1.29

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	1.45 mg/ml ; 0.00957 mol/l
Class :	Soluble
Log S (Ali) :	-2.25
Solubility :	0.854 mg/ml ; 0.00565 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.1
Solubility :	1.21 mg/ml ; 0.008 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.11

Safety of [ 4518-10-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 4518-10-9 ]

* 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 [ 4518-10-9 ]
Downstream synthetic route of [ 4518-10-9 ]

[ 4518-10-9 ] Synthesis Path-Upstream 1~2

1
[ 4518-10-9 ]
[ 67-64-1 ]
[ 184150-96-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With palladium diacetate; copper(II) acetate monohydrate In dimethyl sulfoxide at 80℃; for 48 h; Sealed tube; Inert atmosphere	prepared a degass ed mixture of compound LVI (10.0 g, 0.061 mol) and copper(II) acetate 10 monohydrate (36.2 g, 0.182 mol) in dimethyls ulfoxide (50 mL). To the flask was added acetone (100 mL), followed by palladium(II) acetate (0.270 g, 0.001 mol), and the resulting reaction mixture was heated at 80 °C for 48 h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite and the filtrate w as diluted with water (80 mL). The aqueous mixture w as extracted with ethyl acetate (3 x 100 mL) and the 148 of 363 {//-- DRAFT --//4069/3020WO/00228726/v2} 4069.3020 WO combined organic extracts were dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain the crude product mixture, which was purified by silica gel chromatography using a gradient of 5-7percent ethyl acetate in hexanes as the eluant to affod LVII (4.8 g, 83percent) as a pale yellow solid.¹H NMR (400 MHz, CDCl₃) δ 8.26 (brs, 5 1H), 8.04 (s, 1H), 7.77 (dd, J= 8.3, 3.4 Hz, 1H), 7.50 (d, J= 8.3 Hz, 1H), 6.26 (s, 1H), 3.92 (s, 3H), 2.47 (s, 3H); MS (ESI, positive mode) m/z 190 (MH⁺).

Reference： [1] Patent: WO2015/73528, 2015, A1, . Location in patent: Page/Page column 148-149

2
[ 4518-10-9 ]
[ 209459-11-0 ]

Reference： [1] Patent: WO2009/104155, 2009, A1,

[ 4518-10-9 ] Synthesis Path-Downstream 1~10

1
[ 4518-10-9 ]
[ 151-50-8 ]
[ 13531-48-1 ]

Reference： [1]Chemische Berichte,1938,vol. 71,p. 335,338

2
[ 4518-10-9 ]
[ 33142-21-1 ]
3-(2-ethoxycarbonyl-2-chloro-vinylamino)-benzoic acid methyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society,1950,p. 3345

3
[ 4518-10-9 ]
[ 75-87-6 ]
[ 153072-43-6 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2236 - 2242

4
[ 4518-10-9 ]
[ 1204-06-4 ]
(E)-3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	EXAMPLE 4: Preparation of 3- (3-liY-indol-3-yl-acryloylamino) - benzoic acid methyl ester; In 5.0 mL of dimethylformamide were dissolved 3-(lif- indol-3-yl) -acrylic acid (150 mg, 0.8 mmol) and 3-amino benzoic acid methyl ester (218 mg, 1.44 mmol), followed by the addition of ethylenedichloride (230 mg, 1.2 mmol), N- hydroxybenzotriazole (163 mg, 1.2 mmol), and N, N- diisopropylethylamine (0.21 ml, 1.2 mmol). The resulting solution was stirred at room temperature and mixed with ethyl acetate and an aqueous sodium salt solution. The organic layer was dried over anhydrous magnesium sulfate. After the <n="27"/>filtration and concentration of the residue, the concentrate was purified using silica gel column chromatography (n-hexane : ethyl acetate : methanol = 9:3:1) to produce the subject compound (4) as a yellow solid (102 mg, 38%) . 1H-NMR (CDCl3, 300Hz): 8.90 (IH, s, NH), 8.21 (IH, s, NH), 7.86-8.03 (4H, m, aromatic), 7.76 (IH, d, J = 8.1 Hz aromatic), 7.36-7.41 (3H, m, aromatic), 7.20 (2H, m, aromatic), 6.60 (2H, d, J = 15.3 Hz, aromatic), 3.88 (3H, s, OCH3).
	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	1-3. Synthesis of low-molecular-weight compound ID-52 (8a) Among the above-described low-molecular-weight compounds, ID-52 (3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester (8a)) was prepared in the following manner. Trans-3-indoleacrylic acid (7a, 150 mg, 0.8 mmol) and 3-amino-benzoic acid methyl ester (6a, 218 mg, 1.44 mmol) were dissolved in DMF, and 1-[3-(dimethyamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 230 mg, 1.2 mmol), hydroxy-7-azabenotriazole (HOAT, 163 mg, 1.2 mmol) and N,N-diisopropylethylamine (DIPEA, 0.21 mL, 1.2 mmol) were added to the solution to cause a coupling reaction. The reaction solution was stirred overnight at room temperature. Then, the resulting material was separated and purified to obtain 3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester (ID-52) as a yellow solid. 1H NMR (CDCl3, 300 MHz) d = 8.90 (s, 1H), 8.21 (s, 1H), 7.86-8.03 (m, 4H), 7.76 (d, J = 8.1 Hz, 1H), 7.36-7.41 (m, 3H), 7.20 (m, 2H), 6.60 (d, J = 15.3 Hz, 2H), 3.88 (s, 3H).

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 849 - 858
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 12509 - 12513
Angew. Chem.,2012,vol. 124,p. 12677 - 12681,5
[3]Patent: WO2008/39007,2008,A1 .Location in patent: Page/Page column 25-26
[4]Patent: EP2774918,2014,A1 .Location in patent: Paragraph 0126; 0137-0138

5
[ 4518-10-9 ]
[ 1878-91-7 ]
[ 303794-33-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	<Example 15> 3-[2-(4-bromo-phenoxy)-acetylamino]-benzoic acid methyl esterTo a solution of the <strong>[1878-91-7]4-bromophenoxy acetic acid</strong> (139 mg, 0.6 mmol) and amine (76 mg, 0.5 mmol) in DMF (5.0 mL) were added EDCHCl (144 mg, 0.75 mmol), HOBT (101 mg, 0.75 mmol), and DIPEA (0.13 mL, 0.75 mmol). The reaction mixture was stirred at room temperature overnight, and then partitioned between Ethyl acetat and brine. The organic phase was dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (n-Hexane : Ethyl acetat : MeOH = 12 : 3: 1) gave 3-[2-(4-bromo-phenoxy)- acerylamino]-benzoic acid methyl ester as a white solid (138 mg, 76% yield). :. . 1H-NMR (CDCl3,.300Hz). . 8.32 (IH5 S5MI)5 8.06 (IH5 m, aromatic)5-7.99 (IH5 m5 aromatic), 7.84.(IH5 m, aromatic), 7.42-7.47 (3H5 m, aromatic), 6.89 (2H, m, aromatic), 4.59 (2H, s, OCH2CO), 3.92 (3H, s, OCH3).
76%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	To a solution of the <strong>[1878-91-7]4-bromophenoxy acetic acid</strong> (139 mg, 0.6 mmol) and amine (76 mg, 0.5 mmol) in DMF (5.0 mL) were added EDCHCl (144 mg, 0.75 mmol), HOBT (101 mg, 0.75 mmol), and DIPEA (0.13 mL, 0.75 mmol). The reaction mixture was stirred at room temperature overnight and then partitioned between Ethyl acetate and brine. The organic phase was dried (anhydrous MgSO4), and concentrated. Purification by silica gel column chromatography (n-Hexane:Ethyl acetate:MeOH=12:3:1) gave 3-[2-(4-bromo-phenoxy)-acetylamino]-benzoic acid methyl ester as a white solid (138 mg, 76% yield). 1H-NMR (CDCl3, 300 Hz) 8.32 (1H, s, NH), 8.06 (1H, m, aromatic), 7.99 (1H, m, aromatic), 7.84 (1H, m, aromatic), 7.42-7.47 (3H, m, aromatic), 6.89 (2H, m, aromatic), 4.59 (2H, s, OCH2CO), 3.92 (3H, s, OCH3).
56%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 48h;Inert atmosphere;	EDCI (1.5 eq.) and HOBt (1.5 eq.) were added to a solution of (4-bromo-phenoxy)-acetic acid 2 (1.0 eq.), 3-amino-benzoic acid methyl ester (1.5 eq.), and DIPEA (1.5 eq.) in DMF, and the reaction mixture was stirred for 48 h at RT. After evaporation of the DMF under reduced pressure, the reaction mixture was diluted with AcOEt and sequentially washed with 0.1 M HCl solution, aqueous sodium bicarbonate, and brine and dried over anhydrous MgSO4. The solvent was filtered and evaporated under reduced pressure to produce a crude solid, which was washed several times with diethyl ether to give the pure desired compound 3 (56% yield). Rf = 0.73 (n-hexane:AcOEt:MeOH = 6:3:1); NMR 1H (CDCl3, 300 MHz), delta (ppm): 3.92 (s, 3H, -OCH3), 4.59 (s, 2H, -OCH2CO-), 6.89 (m, 2H, ArH), 7.42-7.47 (m, 3H, ArH), 7.84 (m, 1H, ArH), 7.99 (m, 1H, ArH), 8.06 (1H, m, ArH), and 8.32 (1H, s, -NH-). Data consistent with the literature 3.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1675 - 1684
[2]Patent: WO2008/4798,2008,A1 .Location in patent: Page/Page column 29
[3]Patent: US2009/306078,2009,A1 .Location in patent: Page/Page column 25
[4]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 7401 - 7406
[5]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 806 - 810

6
[ 79-16-3 ]
[ 4518-10-9 ]
[ 79-37-8 ]
[ 5985-24-0 ]
[ 196103-48-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane;	a N-(3-carbomethoxyphenyl)-2-hydroxy-5-carbomethoxybenzamide STR28 Methyl 4-hydroxyisophthalate (1.0 g) and oxalyl chloride (2.2 ml) were stirred together for 18 h in dry dichloromethane containing one drop of dimethylformamid. Removal of solvent gave a white solid which was dissolved in dichloromethane (30 ml) and added to a solution of methyl 3-aminobenzoate (0.8 g) in dichloromethane (30 ml) and pyridine (6.1 ml) at 0° C. After 18 h this was poured into dilute hydrochloric acid and extracted to give a yellow foam (1.7 g). 1 H-NMR (CDCl3) delta: 3.84 (6H,s), 6.8-8.8 (7H,m), 10.7 (2H,br).

Reference： [1]Patent: US5872280,1999,A

7
[ 4518-10-9 ]
[ 1204-06-4 ]
3-[3-(1H-indol-3-yl)acrylamido]benzoic acid [ No CAS ]

Reference： [1]Patent: US2015/159142,2015,A1

8
[ 4518-10-9 ]
[ 183673-71-4 ]
C₁₉H₂₇N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In dichloromethane; at -15 - 20℃;Inert atmosphere;	General procedure: To a suspension of carboxylic acid (100mg) and DMAP (6 eq) in DCM (0.2 M) under nitrogen at -15°C was added T3P (3 eq)dropwise over a period of 20 min. The resulting mixture was stirred at -15°Cuntil a solution was obtained (2h) and the aniline (3 eq) was added dropwise.The reaction mixture was stirred at -15 °C for 1h, slowly warmed to roomtemperature and stirred overnight. Saturated aq. NaHCO3 was thenadded and the aqueous layer extracted with EtOAc. The organic phase was washedwith saturated aq. NH4Cl (x 2), NaHCO3 and brine, driedover Na2SO4, filtered and concentrated under vacuum. Theresidue was dissolved in DCM and purified by flash chromatography (DCM/MeOH97/3 to 92/8).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4005 - 4010

9
[ 4518-10-9 ]
[ 871836-51-0 ]
C₁₄H₁₂N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	at 100℃;	10285] A mixture of 4-chloro-1 H-pyrazolo[4,3-c]pyridine(30.6 mg, 0.2 mmol) and methyl 3-aminobenzoate (30.2 mg,0.2 mmol) was heated at 1000 C. overnight. MeOH (2 mE)was added and the resultant was purified by Prep -TEC (ethylacetate/petroleum ether=1/1) to give D-3-03-1-1 (38 mg,71percent) as a white solid.

Reference： [1]Patent: US2016/2227,2016,A1 .Location in patent: Paragraph 0284; 0285

10
[ 4518-10-9 ]
[ 1038509-28-2 ]

Reference： [1]Patent: WO2009/104155,2009,A1

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Isomers

Technical Information

? Acyl Group Substitution ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction ? Vilsmeier-Haack Reaction

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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. 4518-10-9 ] {[proInfo.proName]}

Quality Control of [ 4518-10-9 ]

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Product Details of [ 4518-10-9 ]

Calculated chemistry of [ 4518-10-9 ] Expand+

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Lipophilicity

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Medicinal Chemistry

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Application In Synthesis of [ 4518-10-9 ]

[ 4518-10-9 ] Synthesis Path-Upstream 1~2

[ 4518-10-9 ] Synthesis Path-Downstream 1~10

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Aryls

Esters

Amines

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[ 4518-10-9 ]