286371-49-1

Basic information

• Product Name: 7-Benzyloxy-4-chloro-6-methoxy-quinoline
• Synonyms: 7-Benzyloxy-4-chloro-6-methoxy-quinoline;4-Chloro-6-methoxy-7-benzyloxyquinoline;Quinoline, 4-chloro-6-Methoxy-7-(phenylMethoxy)-;4-chloro-6-methoxy-7-phenylmethoxyquinoline;7-(Benzyloxy)
• CAS NO: 286371-49-1
• Molecular Formula: C₁₇H₁₄ClNO₂
• Molecular Weight: 299.75156
• EINECS: 1592732-453-0
• Mol File: 286371-49-1.mol

Chemical Properties

• Boiling Point: 434.8±40.0 °C(Predicted)
• Appearance: /
• Density: 1.262
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.92±0.30(Predicted)
• CAS DataBase Reference: 7-Benzyloxy-4-chloro-6-methoxy-quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Benzyloxy-4-chloro-6-methoxy-quinoline(286371-49-1)
• EPA Substance Registry System: 7-Benzyloxy-4-chloro-6-methoxy-quinoline(286371-49-1)

Safety Data

• Hazardous Substances Data: 286371-49-1(Hazardous Substances Data)

Usage

Uses

7-(benzyloxy)-4-chloro-6-methoxyquinoline (cas# 286371-49-1) is a useful research chemical.

Synthetic route

4-hydroxy-6-methoxy-7-benzyloxyquinoline (205448-29-9, 849217-23-8) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Stage #1: 7-benzyloxy-4-hydroxy-6-methoxyquinoline With trichlorophosphate for 2h; Heating / reflux; Stage #2: With sodium hydrogencarbonate; sodium carbonate In water at 20℃; pH=8;	95%
With trichlorophosphate for 2h; Heating / reflux;	95%
With trichlorophosphate In toluene at 120℃; for 1.5h;	90%

4-chloro-6-methoxy-7-hydroxyquinoline (205448-31-3) + benzyl bromide (100-39-0) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 2h;	95%

6-methoxy-7-benzyloxy-4(1H)-quinolinone (205448-29-9, 849217-23-8) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Stage #1: 6-methoxy-7-benzyloxy-4(1H)-quinolinone With trichlorophosphate at 110℃; for 3h; Stage #2: With sodium carbonate In chloroform; water Cooling with ice;	94%
With sodium hydroxide; trichlorophosphate In chloroform	21%
With trichlorophosphate In acetonitrile for 6h; Reflux;	174.8 g

1-(2-amino-4-(benzyloxy)-5-methoxyphenyl)ethanone (75665-73-5) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 1.2: 8 h 2.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 1.2: Inert atmosphere 2.1: trichlorophosphate / 10 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h 1.2: 15 h / 20 °C 2.1: trichlorophosphate / 4.33 h / Cooling with ice; Reflux View Scheme

benzyl bromide (100-39-0) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 1 h / 0 °C / pH 7 - 8 3.1: ammonium formate; iron / toluene; water / 103 °C 4.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 4.2: 8 h 5.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 2.25 h / 0 °C 3.1: iron; ammonium acetate / toluene; water / 105 °C 4.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 4.2: Inert atmosphere 5.1: trichlorophosphate / 10 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: nitric acid / dichloromethane / 2 h / -20 - -10 °C 3.1: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 4.1: iron; acetic acid / 2 h / 60 - 90 °C 5.1: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: nitric acid; sulfuric acid / dichloromethane / 1 h / 0 °C / pH 7 - 8 2.1: ammonium formate; iron / toluene; water / 103 °C 3.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 3.2: 8 h 4.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme
Multi-step reaction with 4 steps 1.1: nitric acid; sulfuric acid / dichloromethane / 2.25 h / 0 °C 2.1: iron; ammonium acetate / toluene; water / 105 °C 3.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 3.2: Inert atmosphere 4.1: trichlorophosphate / 10 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: nitric acid / dichloromethane / 2 h / -20 - -10 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 3: iron; acetic acid / 2 h / 60 - 90 °C 4: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme

1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)ethanone (75665-88-2) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonium formate; iron / toluene; water / 103 °C 2.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 2.2: 8 h 3.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: iron; ammonium acetate / toluene; water / 105 °C 2.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 2.2: Inert atmosphere 3.1: trichlorophosphate / 10 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 2: iron; acetic acid / 2 h / 60 - 90 °C 3: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme

1-(3-methoxy-4-hydroxyphenyl)ethanone (498-02-2) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 1 h / 0 °C / pH 7 - 8 3.1: ammonium formate; iron / toluene; water / 103 °C 4.1: sodium methylate / Dimethyl ether / 0.5 h / 20 °C 4.2: 8 h 5.1: trichlorophosphate / toluene / 2 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2.1: nitric acid; sulfuric acid / dichloromethane / 2.25 h / 0 °C 3.1: iron; ammonium acetate / toluene; water / 105 °C 4.1: sodium methylate / 1,2-dimethoxyethane / 0.5 h / Inert atmosphere 4.2: Inert atmosphere 5.1: trichlorophosphate / 10 h / Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 4 h / 20 °C 2.1: nitric acid / dichloromethane / 2 h / -20 - -10 °C 3.1: 5,5-dimethyl-1,3-cyclohexadiene / 15 h / Reflux 4.1: iron; acetic acid / 2 h / 60 - 90 °C 5.1: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme

5-{[(3-(benzyloxy)-4-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6- dione (205448-28-8) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: biphenyl / diphenylether / 1 h / 220 °C / Inert atmosphere 2: trichlorophosphate / 5 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: 1,2-dichloro-benzene / 7 h / 180 °C 2: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: 1,2-dichloro-benzene / 7 h / 180 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme

1-[2-nitro-4-benzyloxy-5-methoxyphenyl]-3-(dimethylamino)prop-2-en-1-one → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: iron; acetic acid / 2 h / 60 - 90 °C 2: trichlorophosphate / acetonitrile / 6 h / Reflux View Scheme

2-(benzyloxy)-1-methoxy-4-nitrobenzene (75167-86-1) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonium chloride; iron / ethanol; water / 1 h / 20 °C / Reflux 2: ethanol / 1 h / Reflux 3: 1,2-dichloro-benzene / 7 h / 180 °C 4: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme
Multi-step reaction with 4 steps 1: iron / ethanol; water / Reflux 2: ethanol / 1 h / 80 °C 3: 1,2-dichloro-benzene / 7 h / 180 °C 4: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme

3-benzyloxy-4-methoxybenzeneamine (61324-40-1) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 1 h / Reflux 2: 1,2-dichloro-benzene / 7 h / 180 °C 3: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme
Multi-step reaction with 3 steps 1: ethanol / 1 h / 80 °C 2: 1,2-dichloro-benzene / 7 h / 180 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme

5-nitroguaiacol (636-93-1) → 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 40 °C 2: ammonium chloride; iron / ethanol; water / 1 h / 20 °C / Reflux 3: ethanol / 1 h / Reflux 4: 1,2-dichloro-benzene / 7 h / 180 °C 5: trichlorophosphate / toluene / 1.5 h / 120 °C View Scheme
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C 2: iron / ethanol; water / Reflux 3: ethanol / 1 h / 80 °C 4: 1,2-dichloro-benzene / 7 h / 180 °C 5: trichlorophosphate / N,N-dimethyl-formamide / 1 h / 100 °C View Scheme

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → 4-chloro-6-methoxy-7-hydroxyquinoline (205448-31-3)

Conditions	Yield
With methanesulfonic acid; trifluoroacetic acid for 3h; Reflux; Inert atmosphere;	100%
Stage #1: 7-(benzyloxy)-4-chloro-6-methoxyquinoline With methanesulfonic acid; trifluoroacetic acid for 3h; Reflux; Stage #2: With sodium hydroxide for 2h; pH=7;	100%
With trifluoroacetic acid at 75℃; for 6h;	95.4%
With hydrogen bromide; acetic acid In water at 80℃; for 3h;	80%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 4-Amino-3-chlorophenol hydrochloride (52671-64-4) → 4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2-chloroaniline (286371-53-7)

Conditions	Yield
With sodium hydride; potassium carbonate In N,N-dimethyl-formamide; mineral oil at 100℃; for 2h; Inert atmosphere;	98%
With dimethyl sulfoxide In methanol; water	66%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → 4-(7-benzyloxy-6-methoxyquinolin-4-yloxy)aniline (516526-32-2)

Conditions	Yield
Stage #1: 4-amino-phenol With sodium methylate In methanol; ISOPROPYLAMIDE at 20℃; for 1h; Stage #2: 7-(benzyloxy)-4-chloro-6-methoxyquinoline In ISOPROPYLAMIDE at 120℃; for 22h;	96%
Multi-step reaction with 2 steps 1.1: 1-methyl-pyrrolidin-2-one / 2 h / 150 °C 2.1: hydrogenchloride; methanol; water / 6 h / Heating / reflux 2.2: pH 12 View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / 5,5-dimethyl-1,3-cyclohexadiene / 140 °C / Inert atmosphere 2: iron; ammonium chloride / ethanol; water / 2 h / 90 °C / Inert atmosphere View Scheme

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 2-fluoro-4-nitrophenol (403-19-0) → 7-benzyloxy-4-(2-fluoro-4-nitro-phenoxy)-6-methyloxyquinoline (479690-03-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In chlorobenzene at 140℃; for 18h;	92%
With N-ethyl-N,N-diisopropylamine In chlorobenzene for 48h; Reflux;	82%
With N-ethyl-N,N-diisopropylamine In 5,5-dimethyl-1,3-cyclohexadiene at 140℃;	81%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + ethyl 1-[(3-fluoro-4-hydroxyphenyl)carbamoyl]cyclopropane-1-carboxylate → ethyl 1-[[3-fluoro-4-[[6-methoxy-7-benzyloxyquinolin-4-yl]oxy]phenyl]carbamoyl]cyclopropane-1-carboxylate

Conditions	Yield
With dmap at 160℃; for 4h;	90.5%

4-nitro-phenol (100-02-7) + 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → 7-(benzyloxy)-6-methoxy-4-(4-nitrophenoxy)quinoline (417725-03-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In xylene for 12h; Reflux;	84.3%
In chlorobenzene for 16h; Reflux;	62.4%
In chlorobenzene for 20h; Reflux;	201.8 g

1-(2-fluoro-3-hydroxy-6-nitrophenyl)propan-2-one (649736-31-2) + 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → 1-(3-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-2-fluoro-6-nitrophenyl)propan-2-one (1210828-42-4)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 100℃;	84%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 3-fluoro-4-nitrophenol (394-41-2) → 7-(benzyloxy)-4-(3-fluoro-4-nitrophenoxy)-6-methoxyquinoline (286371-58-2)

Conditions	Yield
In chlorobenzene at 120℃; for 21h;	82%
Stage #1: 7-(benzyloxy)-4-chloro-6-methoxyquinoline; 3-fluoro-4-nitrophenol In chlorobenzene at 120℃; for 21h; Stage #2: With sodium hydroxide In chloroform; water; chlorobenzene at 20℃;	82%
With N-ethyl-N,N-diisopropylamine In chlorobenzene at 140℃; for 15h;	50%
With sodium hydroxide In chloroform; chlorobenzene	47%
In chlorobenzene for 16h; Reflux;

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + methyl-phenyl-thioether (100-68-5) → 4-chloro-6-methoxy-7-hydroxyquinoline (205448-31-3)

Conditions	Yield
With sodium hydroxide; methanesulfonic acid In hexane; trifluorormethanesulfonic acid	75%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 4-amino-2-fluorophenol (399-96-2) → 4-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorobenzenamine (479690-04-5)

Conditions	Yield
Stage #1: 4-amino-2-fluorophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 7-(benzyloxy)-4-chloro-6-methoxyquinoline In N,N-dimethyl-formamide; mineral oil at 100℃; for 30h;	73%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + N-(3-fluoro-4-hydroxyphenyl)-N'-(2-phenylethyl)ethanediamide (849217-56-7) → N-{4-[(7-benzyloxy-6-methoxyquinolin-4-yl)oxy]-3-fluorophenyl}-N'-(2-phenylethyl)ethanediamide

Conditions	Yield
With dmap; bromobenzene for 6h; Heating / reflux;	61%
With dmap In bromobenzene for 6h; Heating / reflux;	61%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + para-nitrobenzenethiol (1849-36-1) → 7-(benzyloxy)-6-methoxy-4-((4-nitrophenyl)thio)quinoline

Conditions	Yield
In chlorobenzene for 16h; Reflux;	60.1%

6-hydroxy-N-methyl-1-naphthalenecarboxamide (847802-91-9) + 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → 6-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-N-methyl-1-naphthamide (1058137-70-4)

Conditions	Yield
With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide; acetylacetone at 120℃; for 24h; Reagent/catalyst; Solvent; Temperature; Time; Concentration;	58%
With dmap In 1,4-dioxane for 72h; Product distribution / selectivity; Heating / reflux;

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + meta-nitrophenol (554-84-7) → C23H18N2O5

Conditions	Yield
In chlorobenzene for 16h; Reflux;	52.4%
In chlorobenzene for 18h; Reflux;

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 2,5-dimethyl-4-amino phenol (3096-71-7) → 4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,5-dimethylaniline (286371-50-4)

Conditions	Yield
With dimethyl sulfoxide In methanol; water	52%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 4-amino-2,3-dimethylphenol (3096-69-3) + sodium hydrogencarbonate (144-55-8) → 4-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]oxy}-2,3-dimethylaniline (286371-56-0)

Conditions	Yield
With dimethyl sulfoxide	49%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 2-phenyl-[1,8]naphthyridin-3-ol (666735-37-1) → 3-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-2-phenyl-[1,8]naphthyridine

Conditions	Yield
With dmap In 1,2-dichloro-benzene at 140℃; for 20h;	42%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 3,4-dihydro-2H-benzo[b][1,4]oxazin-7-ol hydrochloride (1149370-96-6) → 7-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1149370-97-7)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 109h;	40.5%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + thiophene-2-carboxylic acid (4-hydroxy-phenyl)-amide (98902-53-5) → thiophene-2-carboxylic acid [4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-amide (914490-48-5)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 5h;	36%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + p-benzoylaminophenol (15457-50-8) → N-[4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-benzamide (914200-89-8)

Conditions	Yield
at 140℃; for 3h;	32%
at 140℃; for 3h; Product distribution / selectivity;	32%
at 140℃; for 3h;	32%
In N,N-dimethyl-formamide at 145℃; for 7h; Product distribution / selectivity;	28%

4-fluoro-2-methyl-1H-indol-5-ol (288385-88-6) + 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → 7-(benzyloxy)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxyquinoline (1210828-43-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 16h; Inert atmosphere;	27%
With dmap In 1,4-dioxane for 72h; Reflux;

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 2-(4-hydroxyphenyl)-1-phenylethan-1-one (6420-90-2) → 2-[4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-1-phenyl-ethanone (914490-65-6)

Conditions	Yield
In N,N-dimethyl-formamide at 145℃; for 5h;	21%

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + sodium 4-aminophenolate (15267-98-8) → 4-(7-benzyloxy-6-methoxyquinolin-4-yloxy)aniline (516526-32-2)

Conditions	Yield
In ISOPROPYLAMIDE at 120℃; for 22h;

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 4-acetaminophenol (103-90-2) → N-[4-(7-benzyloxy-6-methoxy-quinolin-4-yloxy)-phenyl]-acetamide (914490-52-1)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 150℃; for 2h;

7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) + 6-hydroxy-1-naphthoic acid (2437-17-4) → 6-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-1-naphthoic acid (1044676-75-6)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 130℃; for 5h;

indol-5-ol (1953-54-4) + 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → C25H20N2O3 (1058157-84-8)

Conditions	Yield
With dmap In 1,4-dioxane for 72h; Heating / reflux;

5-amino-1H-indole (5192-03-0) + 7-(benzyloxy)-4-chloro-6-methoxyquinoline (286371-49-1) → 4-(1H-indol-5-ylamino)-7-benzyloxy-6-methoxy-quinoline (1058157-22-4)

Conditions	Yield
In isopropyl alcohol for 1h; Heating / reflux;

Upstream product

• 636-93-1 5-nitroguaiacol 
• 61324-40-1 3-benzyloxy-4-methoxybenzeneamine 
• 75167-86-1 2-(benzyloxy)-1-methoxy-4-nitrobenzene 
• 205448-28-8 5-{[(3-(benzyloxy)-4-methoxyphenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6- dione 
• 205448-31-3 4-chloro-6-methoxy-7-hydroxyquinoline 
• 100-39-0 benzyl bromide 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 75665-88-2 1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)ethanone 
• 1835-11-6 4-benzyloxy-3-methoxyacetophenone 
• 75665-73-5 1-(2-amino-4-(benzyloxy)-5-methoxyphenyl)ethanone 
• 205448-29-9 6-methoxy-7-benzyloxy-4(1H)-quinolinone 
• 205448-29-9 7-benzyloxy-4-hydroxy-6-methoxyquinoline 

Downstream Products

• 861881-04-1 4-chloro-7-(3-chloropropoxy)-6-methoxyquinoline 
• 1622396-60-4 C₂₆H₃₀ClN₃O₄ 
• 1622396-74-0 C₂₄H₂₀FN₃O₄ 
• 1622396-75-1 C₃₀H₂₉ClFN₃O₆ 
• 1622396-76-2 C₃₀H₃₀FN₃O₆ 
• 1622396-77-3 C₂₈H₂₅ClFN₃O₆ 
• 1622396-78-4 C₂₈H₂₆FN₃O₆ 
• 1622343-43-4 C₃₅H₃₆ClFN₄O₆ 
• 1622385-35-6 C₃₅H₃₇FN₄O₆ 
• 1622343-31-0 C₃₀H₂₉ClFN₃O₆ 
• 1622342-89-5 C₃₁H₂₅ClFN₃O₄ 
• 1622342-97-5 C₂₄H₁₉ClFN₃O₄ 
• 1622343-07-0 C₃₄H₃₆ClFN₄O₅ 

Relevant articles and documents

Discovery of 1,6-naphthyridinone-based MET kinase inhibitor bearing quinoline moiety as promising antitumor drug candidate

A series of 1,6-naphthyridinone-based MET kinase inhibitors bearing quinoline moiety in block A were designed and synthesized based on the structures of Cabozantinib and our reported compound IV. Extensive SAR and DMPK studies led to the identification of 20j, a potent and orally bioavailable MET kinase inhibitor with favorable kinase selectivity. More importantly, 20j exhibited statistically significant tumor growth inhibition (Tumor growth inhibition/TGI of 131%, 4/6 partial regression/PR) in the U-87 MG xeograft model, which is superior to that of Cabozantinib (TGI of 97%, 2/6 PR), and significantly better than that of compound IV (TGI of 15%, 0/6 PR) at the same dose (12.5 mg/kg). Combined with favorable in vitro potency, kinase selectivity, pharmacokinetic profile and in vivo efficacy, the promising antitumor drug candidate 20j has subsequently advanced into preclinical research.

Heterocyclic compound, preparation method and application thereof

The invention relates to a heterocyclic compound in the technical field of medicines. The compound is represented by a structural general formula I or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, X, Y, Z, Cy1, Cy2, m, n and t have the meanings given in the specification; in addition, the invention also discloses an application of the compound and the pharmaceuticallyacceptable salt thereof in preparation of drugs for treating diseases caused by abnormal high expression of tyrosine kinase, especially application in preparation of drugs for treating and preventingcancers.

CARBAMATE AND UREA COMPOUNDS AS MULTIKINASE INHIBITORS

The present disclosure describes carbamate and urea compounds as novel multikinase inhibitors and methods for preparing them. The pharmaceutical compositions comprising such multikinase inhibitors and methods of using them for treating cancer, infectious diseases, and other disorders associated with kinases are also described.

Naphthyridine compound and pharmaceutical composition as well as applications thereof

The invention relates to the field of biological medicines and discloses a naphthyridine compound and a pharmaceutical composition as well as applications thereof. The naphthyridine compound has a structure shown in a formula (I) or a stereisomer, a geometric isomer, a tautomer, nitric oxide, hydrate, solvate, metabolite, a pharmaceutically acceptable salt or a prodrug. The naphthyridine compound disclosed by the invention has an anti-tumor effect which is obviously superior to the anti-tumor effect of the prior art. And moreover, the naphthyridine compound disclosed by the invention can treat diseases mediated by protein kinase.

Quinoline or quinazoline derivatives as well as preparation method and application thereof

The invention relates to quinoline or quinazoline derivatives as well as a preparation method and an application thereof, namely, the quinoline or quinazoline derivatives shown as the formula I as well as pharmaceutically acceptable salts and hydrates or prodrugs of the quinoline or quinazoline derivatives. The structure is shown in the specification, wherein A1, A2, R1, R2, R3, R4, R5, R6, X, Y, Z, M, W, Cy1, Cy2, m and n are defined in the specification. The invention further relates to the function of the compounds in the general formula I for inhibiting MET kinase and the application of the compounds as well as the pharmaceutically acceptable salts and hydrates of the compounds in preparation of drugs for treating diseases caused by abnormal high expression of the MET kinase, in particular to the application in preparation of drugs for treating and preventing cancer.

A alkyne generation quinoline derivatives and its preparation and use

The invention discloses alkynylquinoline derivatives, and a preparation method and application thereof. The acetylenoquinoline derivatives are alkynylquinoline compounds as shown in a general formula I which is described in the specification and pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof. The invention also provides the preparation method for the derivatives and relates to inhibition activity of the compounds as shown in the formula I to a variety of protein tyrosine kinases (e.g. C-Met and VEGFR). Thus, the compounds can be used as anticancer drugs for treatment of human cancers.

Aryloxy quinoline derivatives and their use in therapy

Disclosed herein are aryloxy quinolines derivatives,and the said compounds are compounds of formula (I) or pharmaceutically acceptable salts thereof or solvates, wherein R1, R2, R3, R4, m, n, X, Z, Ar are defined detailedly in the description. Furthermore, medicaments comprising said compounds or salts as active components and the use for treating conditions and disorders relating to protein-tyrosine kinase receptors, especially c-Met, VEGFR are also described.

THERAPEUTIC COMPOUNDS AND USES THEREOF

Described herein are compounds of Formula (I) or Formula (VI), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Also provided are particles (e.g., nanoparticles) comprising compounds of Formula (I) or Formula (VI) and pharmaceutical compositions thereof that are mucus penetrating. Methods of using the compounds or pharmaceutical compositions thereof for treating diseases are also provided.

SUBSTITUTED QUINOLINE COMPOUNDS AND METHODS OF USE

The present invention provides novel substituted quinoline compounds, pharmaceutical acceptable salts and formulations thereof useful in modulating the protein tyrosine kinase activity, and in modulating cellular activities such as proliferation, differentiation, apoptosis, migration and invasion. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of hyperproliferative disorders in mammals, especially humans.

QUINOLINYLOXYPHENYLSULFONAMIDES

The present invention relates to quinolinyloxyphenylsulfonamides and stereoisomeric forms, solvates, hydrates and/or pharmaceutically acceptable salts of these quinolinyloxyphenylsulfonamide compounds as well as pharmaceutical compositions containing at least one of these compounds together with at least one pharmaceutically acceptable carrier, excipient and/or diluent. Said quinolinyloxyphenylsulfonamides are useful for prophylaxsis, treatment and/or after-treatment of hyperproliferative disorders, such as cancer, tumors and particularly cancer metastases.