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inquiry(6-chloro-4-(methylamino)pyridin-3-yl)methanol
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
With manganese(IV) oxide In dichloromethane at 20℃; Inert atmosphere; | 93% |
With manganese(IV) oxide In dichloromethane at 20℃; Inert atmosphere; | 93% |
With manganese(IV) oxide In dichloromethane at 30℃; for 6h; | 87% |
2,4-dichloro-5-pyridinecarboxaldehyde
methylamine
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
In tetrahydrofuran at 45℃; for 48h; | 93% |
ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 3h; Stage #2: With manganese(IV) oxide In dichloromethane at 20℃; for 2h; | 84% |
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 °C 1.2: 20 °C 2.1: manganese(IV) oxide / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 2: manganese(IV) oxide / dichloromethane / 6 h / 30 °C View Scheme |
4,6-dihydroxynicotinic acid ethyl ester
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 3 h / 110 °C 2.1: acetonitrile; water / 3.5 h / 0 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 °C 3.2: 20 °C 4.1: manganese(IV) oxide / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: trichlorophosphate / 2 h / Reflux 2: water; acetonitrile / 8 h / 0 - 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 4: manganese(IV) oxide / dichloromethane / 6 h / 30 °C View Scheme | |
Multi-step reaction with 4 steps 1: trichlorophosphate / 2 h / Reflux 2: water; acetonitrile / 8 h / 0 - 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 4: manganese(IV) oxide / dichloromethane / 6 h / 30 °C View Scheme |
diethyl 1,3-acetonedicarboxylate
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: acetic anhydride / 1.5 h / 120 °C 1.2: 0 °C / Cooling 1.3: pH < 5 2.1: trichlorophosphate / 3 h / 110 °C 3.1: acetonitrile; water / 3.5 h / 0 - 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 °C 4.2: 20 °C 5.1: manganese(IV) oxide / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: orthoformic acid triethyl ester / 2 h / 120 °C 1.2: 0 - 20 °C 2.1: trichlorophosphate / 2 h / Reflux 3.1: water; acetonitrile / 8 h / 0 - 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 5.1: manganese(IV) oxide / dichloromethane / 6 h / 30 °C View Scheme | |
Multi-step reaction with 5 steps 1: 2 h / 120 °C 2: trichlorophosphate / 2 h / Reflux 3: water; acetonitrile / 8 h / 0 - 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 5: manganese(IV) oxide / dichloromethane / 6 h / 30 °C View Scheme |
ethyl 4,6-dichloronicotinate
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: acetonitrile; water / 3.5 h / 0 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 °C 2.2: 20 °C 3.1: manganese(IV) oxide / dichloromethane / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: water; acetonitrile / 8 h / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 3: manganese(IV) oxide / dichloromethane / 6 h / 30 °C View Scheme | |
Multi-step reaction with 3 steps 1: water; acetonitrile / 8 h / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 3: manganese(IV) oxide / dichloromethane / 6 h / 30 °C View Scheme |
2,4-dichloro-5-hydroxymethylpyridine
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: manganese(IV) oxide / chloroform / 12 h / 75 °C 2: tetrahydrofuran / 48 h / 45 °C View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
4-fluoro-2-methyl-5-nitroaniline
2-chloro-5-((4-fluoro-2-methyl-5-nitrophenylamino)methyl)-N-methylpyridin-4-amine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In acetic acid at 20℃; | 100% |
cycl-isopropylidene malonate
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
7-chloro-1-methyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylic acid
Conditions | Yield |
---|---|
With piperidine; acetic acid In ethanol at 20℃; for 2.33333h; Reflux; | 99% |
With piperidine; acetic acid at 20℃; for 2.33333h; Reflux; | 99% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
GlyOEt*HCl
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h; | 92% |
ethyl 2-(5-amino-2-chlorophenyl)acetate
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
3-(5-amino-2-chlorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; | 83% |
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 4h; | 83% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
methyl (2-chlorophenyl)acetate
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide at 20℃; for 2h; Inert atmosphere; | 75% |
With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide at 20℃; for 2h; Inert atmosphere; | 75% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
ethyl 2-(5-amino-4-fluoro-2-methylphenyl)acetate
3-(5-amino-4-fluoro-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide at 20℃; for 2h; | 69% |
With 40% potassium fluoride/alumina In N,N-dimethyl acetamide at 20℃; for 2h; | 69% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
ethyl 2-(5-amino-2,4-difluorophenyl)acetate
3-(5-amino-2,4-difluorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide for 0.166667h; | 68% |
With 40% potassium fluoride/alumina In N,N-dimethyl acetamide for 0.166667h; | 68% |
2,6-difluoro-3,5-dimethoxybenzeneamine
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,6-difluoro-3,5-dimethoxybenzeneamine With sodium tris(acetoxy)borohydride; trifluoroacetic acid at 0℃; for 0.0333333h; Stage #2: 6-chloro-4-(methylamino)pyridine-3-carbaldehyde In dichloromethane at 20℃; | 68% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate
3-(5-amino-2-bromo-4-fluoro-phenyl)-7-chloro-1-methyl-1H-[1,6]naphthyridin-2-one
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide at 20℃; for 0.166667h; | 67% |
With potassium fluoride on basic alumina In N,N-dimethyl acetamide at 20℃; for 0.166667h; | 67% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide at 20℃; for 2h; | 67% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
ethyl 2-(5-amino-2-chloro-4-fluorophenyl)acetate
3-(5-amino-2-chloro-4-fluorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
With aluminum oxide; potassium fluoride In N,N-dimethyl acetamide at 20℃; for 1h; | 60% |
With 40% potassium fluoride/alumina In N,N-dimethyl acetamide at 20℃; for 1h; | 60% |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
methyl 2-(5-amino-2-methylphenyl)acetate
3-(5-amino-2-methylphenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; | |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
methyl 3-((methoxycarbonyl)methyl)-4-methylbenzoate
C18H15ClN2O3
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
methyl 2-(5-amino-2-methylphenyl)acetate
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
ethyl (triphenylphosphoranylidene)acetate
(E)-ethyl-3-(6-chloro-4-(methylamino)pyridin-3-yl)acrylate
Conditions | Yield |
---|---|
In tetrahydrofuran for 16h; Reflux; |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 16 h / Reflux 2: 1-methyl-pyrrolidin-2-one; water / 0.58 h / 150 °C / Microwave irradiation View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
3-bromo-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran / 16 h / Reflux 2: 1-methyl-pyrrolidin-2-one; water / 0.58 h / 150 °C / Microwave irradiation 3: pyridine; Phenylselenyl bromide / dichloromethane / 6 h / 39 °C View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
3-(tributylstannyl)-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: tetrahydrofuran / 16 h / Reflux 2: 1-methyl-pyrrolidin-2-one; water / 0.58 h / 150 °C / Microwave irradiation 3: pyridine; Phenylselenyl bromide / dichloromethane / 6 h / 39 °C 4: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 48 h / 80 - 90 °C / Inert atmosphere; Sealed tube View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
3-(2-(N,N-bis-(t-butoxycarbonyl)amino)-3,5-difluoropyridin-4-yl)-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: tetrahydrofuran / 16 h / Reflux 2: 1-methyl-pyrrolidin-2-one; water / 0.58 h / 150 °C / Microwave irradiation 3: pyridine; Phenylselenyl bromide / dichloromethane / 6 h / 39 °C 4: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 48 h / 80 - 90 °C / Inert atmosphere; Sealed tube 5: copper(l) iodide; triphenyl-arsane / tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 48 h / 60 °C / Inert atmosphere; Sealed tube View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
3-(2-amino-3,5-difluoropyridin-4-yl)-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: tetrahydrofuran / 16 h / Reflux 2: 1-methyl-pyrrolidin-2-one; water / 0.58 h / 150 °C / Microwave irradiation 3: pyridine; Phenylselenyl bromide / dichloromethane / 6 h / 39 °C 4: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 48 h / 80 - 90 °C / Inert atmosphere; Sealed tube 5: copper(l) iodide; triphenyl-arsane / tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 48 h / 60 °C / Inert atmosphere; Sealed tube 6: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
N-(4-(7-(ethylamino)-1-methyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-3,5-difluoropyridin-2-yl)propane-1-sulfonamide
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: tetrahydrofuran / 16 h / Reflux 2: 1-methyl-pyrrolidin-2-one; water / 0.58 h / 150 °C / Microwave irradiation 3: pyridine; Phenylselenyl bromide / dichloromethane / 6 h / 39 °C 4: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 48 h / 80 - 90 °C / Inert atmosphere; Sealed tube 5: copper(l) iodide; triphenyl-arsane / tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 48 h / 60 °C / Inert atmosphere; Sealed tube 6: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 7: triethylamine / dichloromethane / 16 h / 0 - 20 °C View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium fluoride; aluminum oxide / N,N-dimethyl acetamide / 1 h / 20 °C 2: 3 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: 40% potassium fluoride/alumina / N,N-dimethyl acetamide / 1 h / 20 °C 2: 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(2-methoxyethylamino)-1,6-naphthyridin-2(1H)-one / 3 h / 180 °C / Inert atmosphere View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium fluoride; aluminum oxide / N,N-dimethyl acetamide / 1 h / 20 °C 2: 3 h / 180 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: 40% potassium fluoride/alumina / N,N-dimethyl acetamide / 1 h / 20 °C 2: 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(2-methoxyethylamino)-1,6-naphthyridin-2(1H)-one / 3 h / 180 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / Reflux View Scheme |
6-chloro-4-(methylamino)pyridine-3-carbaldehyde
7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chlorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 4 h / 180 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 180 °C / Inert atmosphere View Scheme |
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