[ CAS No. 35654-56-9 ] {[proInfo.proName]}

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Quality Control of [ 35654-56-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 35654-56-9 ]

SDS Specification

Alternatived Products of [ 35654-56-9 ]

Product Details of [ 35654-56-9 ]

CAS No. :	35654-56-9	MDL No. :	MFCD07778437
Formula :	C₁₁H₁₀ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WRVHQEYBCDPZEU-UHFFFAOYSA-N
M.W :	223.66	Pubchem ID :	459610
Synonyms :

Calculated chemistry of [ 35654-56-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.18
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.74
TPSA :	31.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.48
Log Po/w (XLOGP3) :	2.76
Log Po/w (WLOGP) :	2.91
Log Po/w (MLOGP) :	1.72
Log Po/w (SILICOS-IT) :	3.05
Consensus Log Po/w :	2.58

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.33
Solubility :	0.105 mg/ml ; 0.000471 mol/l
Class :	Soluble
Log S (Ali) :	-3.07
Solubility :	0.189 mg/ml ; 0.000844 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.58
Solubility :	0.0059 mg/ml ; 0.0000264 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 35654-56-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 35654-56-9 ]

* 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 [ 35654-56-9 ]
Downstream synthetic route of [ 35654-56-9 ]

[ 35654-56-9 ] Synthesis Path-Upstream 1~2

1
[ 35654-56-9 ]
[ 666734-51-6 ]

Reference： [1] Patent: CN104788372, 2018, B, . Location in patent: Paragraph 0136; 0137

2
[ 35654-56-9 ]
[ 394-41-2 ]
[ 228559-87-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1359 - 1366
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 14, p. 6277 - 6292
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 875 - 879
[4] Patent: US2008/4273, 2008, A1, . Location in patent: Page/Page column 72

[ 35654-56-9 ] Synthesis Path-Downstream 1~9

1
[ 35654-56-9 ]
[ 19499-93-5 ]
4-(2,3-dimethyl-4-nitro-phenoxy)-6,7-dimethoxy-quinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 875 - 879

2
[ 35654-56-9 ]
[ 42019-78-3 ]
(4-Chlorophenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%		Example 41 (4-Chlorophenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanone [37] 4-Chloro-6,7-dimethoxyquinoline (112 mg) and commercially available 4-chlorophenyl 4-hydroxyphenyl ketone (349 mg) were mixed and stirred at 180° C. for 20 minutes. The reaction mixture was purified by thin layer chromatography on silica gel eluding with chloroform/ethyl acetate (5/1) to obtain 26 mg of the title compound (yield: 12percent). 1 H-NMR (CDCl3, 90 MHz): delta 4.03 (s, 3H), 4.07 (s, 3H), 6.66 (d, J=5.3 Hz, 1H), 7.19~7.34 (m, 2H), 7.44~7.56 (m, 4H), 7.71~7.99 (m, 4H), 8.58 (d, J=5.3 Hz, 1H) Mass spectrometry data (FD-MS, m/z): 419 (M+)

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 5117 - 5133
[2]Patent: US6143764,2000,A

3
[ 35654-56-9 ]
[ 84478-72-8 ]
[ 205447-28-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	In pentanol, 2-; at 120℃; for 6h;	EXAMPLE 2 A suspension of 4-chloro-6,7-dimethoxyquinoline (0.2 g, 0.89 mmol) and <strong>[84478-72-8]4-chloro-2-fluoro-5-hydroxyaniline</strong> (173 mg, 1 mmol), (as described in EP 61741 A2), in 2-pentanol (2.5 ml) was heated at 120 C. for 6 hours.. The resulting solid was collected by filtration, washed with isopropanol and then ether and dried under vacuum to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinoline hydrochloride (231 mg, 67%) as a white solid.

Reference： [1]Patent: US6809097,2004,B1 .Location in patent: Page column 37-38

4
[ 35654-56-9 ]
[ 24985-85-1 ]
5-(6,7-dimethoxy-quinolin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With dmap; In o-xylene;Heating / reflux;	Compound 22: Ethyl 5-[(6,7-dimethoxy-4-quinolyl)oxy]-1H-2-indolecarboxylate; 5-Hydroxy-1H-2-indolecarboxylic acid (328 mg) was dissolved in ethanol (10 ml) to prepare a solution. Concentrated sulfuric acid was added to the solution, and the mixture was heated under reflux for 3 hr. The reaction solution was cooled to room temperature, an aqueous sodium hydrogencarbonate solution was then added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel using ethyl acetate-hexane to give ethyl 5-hydroxy-1H-2-indolecarboxylate (336 mg, yield 88%). 4-Chloro-6,7-dimethoxyquinoline (362 mg), ethyl 5-hydroxy-1H-2-indolecarboxylate (277 mg), and 4-dimethylaminopyridine (195 mg) were suspended in o-xylene, and the suspension was heated under reflux overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using ethyl acetate-hexane on silica gel to give the title compound (161 mg, yield 30%). 1H-NMR (CDCl3, 400 MHz): delta 1.43 (t, J = 7.1 Hz, 3H), 4.07 (s, 3H), 4.07 (s, 3H), 4.44 (q, J = 7.1 Hz, 2H), 6.43 (d, J = 5.4 Hz, 1H), 7.18 (dd, J = 2.2 Hz, 9.0 Hz, 1H), 7.24 (m, 1H), 7.47 (s, 1H), 7.50 - 7.52 (m, 2H), 7.64 (s, 1H), 8.46 (d, J = 5.4 Hz, 1H), 9.05 (s, 1H) Mass spectrometric value (ESI-MS, m/z): 393 (M+1)+
	With dmap; In toluene; at 180℃; for 2h;Microwave irradiation;	Example 105; 5- (6, 7-Dimethoxy-quinolin-4-yloxy)- 1H-indole-2-carboxylic acid (3- methoxy-phenyl)-amide; (a) 5- (6, 7-Dimethoxy-quinolin-4-yloxy)-lH-indole-2-carboxylic acid ethyl ester.; A mixture of 4-chloro-6, 7-dimethoxy-quinoline (0.4 g, 1.8 mmol), 5-hydroxy-lH-indole-2- carboxylic acid ethyl ester (0.37 g, 1.8 mmol, Biosynth AG) and DMAP (0.22 g, 1.8 mmol, Aldrich) in toluene (in a microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 180 C for 2 h. The mixture was cooled to RT and diluted with 30 mL of EtOAc. The solution was washed with 10 mL of brine twice, dried over Na2SO4 and concentrated in vacuo. The residue was further purified with silica gel column chromatography (50% to 100% EtOAc in hexanes) to provide a white foam as the desired compound. MS (ESI pos. ion) m/z: 393 (M+H). Calc'd Exact Mass for C22H2oN20s : 392.40.

Reference： [1]Patent: EP1548008,2005,A1 .Location in patent: Page/Page column 65-66
[2]Patent: WO2005/73224,2005,A2 .Location in patent: Page/Page column 74

5
[ 35654-56-9 ]
[ 30992-63-3 ]
1-[5-Benzyloxy-2-(6,7-dimethoxy-quinolin-4-yloxy)-phenyl]-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With dmap; In 1,2-dichloro-benzene; at 130℃; for 10h;	Compound 175: 1-[5-Benzyloxy-2-(6,7-dimethoxy-quinolin-4-yloxy)-phenyl]-ethanone; 2,5-Dihydroxyacetophenone (3.00 g), benzyl bromide (2.48 g), and potassium carbonate (8.16 g) were suspended in acetonitrile (30 ml) to prepare a suspension which was heated under reflux overnight. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give 3-benzyloxy-6-hydroxyacetophenone (1.88 g, yield 39%). 3-Benzyloxy-6-hydroxyacetophenone (1.88 g), 4-chloro-6,7-dimethoxyquinoline (3.43 g), and 4-dimethylaminopyridine (1.41 g) were suspended in o-dichlorobenzene (20 ml) to prepare a suspension which was then stirred at 130C for 10 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (188 mg, yield 6%). 1H-NMR (CDCl3, 400 MHz): delta 2.41 (s, 3H), 3.97 (s, 6H), 5.06 (s, 2H), 6.31 (d, J = 5.2 Hz, 1H), 7.02 (d, J = 8.8 Hz, 1H), 7.13 (dd, J = 8.8 Hz, J = 3.2 Hz, 1H), 7.25 - 7.41 (m, 6H), 7.45 (d, J = 3.2 Hz, 1H), 7.49 (s, 1H), 8.41 (d, J = 5.2 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 430 (M+1)+

Reference： [1]Patent: EP1548008,2005,A1 .Location in patent: Page/Page column 107
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 3326 - 3329

6
[ 35654-56-9 ]
[ 904326-92-7 ]
[ 1119718-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In 1,2-dimethoxyethane; water; at 80℃;	To 100 mL round-bottomed flask was added 4-chloro-6,7-dimethoxyquinoline (0.1125 g, 0.503 mmol), <strong>[904326-92-7]6-fluoro-5-methylpyridin-3-ylboronic acid</strong> (0.1075 g, 0.629 mmol), and trans-dichlorobis(triphenyl-phosphine)palladium (II) (0.0321 g, 0.0402 mmol) in 1,2-dimethoxyethane. An aqueous solution of sodium carbonate (27 g, 257 mmol) was added and the temperature was brought to 80 C. stir overnight. Upon completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, saturated sodium chloride solution, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column (25M), eluding with a gradient of 10% to 70% ethyl acetate in hexane, to provide 4-(6-fluoro-5-methylpyridin-3-yl)-6,7-dimethoxyquinoline (0.059 g).

Reference： [1]Patent: US2009/62277,2009,A1 .Location in patent: Page/Page column 15

7
[ 35654-56-9 ]
[ 5847-59-6 ]
[ 1437323-80-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; In chlorobenzene; at 140℃; for 48h;Inert atmosphere;	A mixture of 4-chloro- 6,7-dimethoxyquinoline (0.82 g, 3.67 mmol), <strong>[5847-59-6]2-bromo-4-nitrophenol</strong> (0.80 g, 3.67 mmol) and 4-dimethylaminopyridine (0.067 g, 0.549 mmol) in chlorobenzene (8 mL) was heated at 140 C for 2 days under an argon atmosphere. The crude product was purified by silica gel column chromatography followed by crystallization from a mixture of CH2CI2, MeOH, ether, and hexane to produce 4-(2-bromo-4-nitrophenoxy)-6,7-dimethoxyquinoline (0.74 z = 406 (M + 1).

Reference： [1]Patent: WO2013/74633,2013,A1 .Location in patent: Page/Page column 77

8
[ 489446-42-6 ]
[ 35654-56-9 ]
tert-butyl (4-(6,7-dimethoxyquinolin-4-yl)benzyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 12h;Inert atmosphere;	[0596] Procedure: To a stirred solution of 4-chloro-6,7-dimethoxyquinoline (0.5 g, 2.242 mmol), (4-((tert-butoxycarbonyl)amino)methyl)phenyl)boronic acid (0.56 g, 2.242 mmol) and potassium carbonate (0.92 g, 6.726 mmol) in 1,4-dioxane ( 10 mL) and water ( 3 mL) was degassed with nitrogen gas for 10 min, then tetrakis(triphenylphosphine)palladium(0) (0.13 g, 0.1121 mmol) was added and heated for 12 h at 100 C. The reaction mixture was cooled to room temperature, filtered through celite bed, the filtrate was dried and concentrated to give crude product. The crude was purified by flash column with silica gel pack and 30% ethyl acetate in hexane as eluent. The pure fractions were collected and concentrated to afford tert-butyl (4-(6,7-dimethoxyquinolin-4-yl)benzyl)carbamate as off white solid (0.62 g, 70%).1HNMR (400 MHz, DMSO-d6): delta 8.69 (d, J = 3.6 Hz, 1H), 7.65- 7.55 (m, 1H), 7.55- 7.50 (m, 2H), 7.50- 7.40 (m, 3H), 7.23 (d, J = 3.6 Hz, 1H), 7.15 (s, 1H), 4.23 (d, J = 4.8 Hz, 2H), 3.94 (s, 3H), 3.73 (s, 3H), 1.40 (s, 9H). LC-MS (ES) m/z = 395.1 [M+H]+ .

Reference： [1]Patent: WO2019/46778,2019,A1 .Location in patent: Paragraph 0596

9
[ 489446-42-6 ]
[ 35654-56-9 ]
tert-butyl (4-(6,7-dimethoxyquinolin-4-yl)benzyl)(methyl)carbamate [ No CAS ]

Reference： [1]Patent: WO2019/46778,2019,A1

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Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Ethers • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Historical Records

Pharmaceutical Intermediates of
[ 35654-56-9 ]

Cabozantinib Intermediates

[ 849217-60-3 ]

N-(4-Fluorophenyl)-N'-(4-hydroxyphenyl)cyclopropane-1,1-dicarboxamide

[ 4101-32-0 ]

4',5'-Dimethoxy-2'-nitroacetophenone

[ 190728-25-7 ]

4-((6,7-Dimethoxyquinolin-4-yl)oxy)aniline

[ 3697-66-3 ]

1-(Ethoxycarbonyl)cyclopropanecarboxylic acid

[ 1131-62-0 ]

1-(3,4-Dimethoxyphenyl)ethanone

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[ 35654-56-9 ]

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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

[ CAS No. 35654-56-9 ] {[proInfo.proName]}

Quality Control of [ 35654-56-9 ]

Related Doc. of [ 35654-56-9 ]

Product Details of [ 35654-56-9 ]

Calculated chemistry of [ 35654-56-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 35654-56-9 ]

[ 35654-56-9 ] Synthesis Path-Upstream 1~2

[ 35654-56-9 ] Synthesis Path-Downstream 1~9

Technical Information

Pharmaceutical Intermediates of [ 35654-56-9 ]

Cabozantinib Intermediates

Related Functional Groups of [ 35654-56-9 ]

Chlorides

Ethers

Related Parent Nucleus of [ 35654-56-9 ]

Quinolines

Precautionary Statements-General

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Storage

Disposal

Physical hazards

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Environmental hazards

Inquiry

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[ 35654-56-9 ]

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[ 35654-56-9 ]

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[ 35654-56-9 ]