3719-45-7

Basic information

• Product Name: 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid
• Synonyms: N(1)-methyl-2-pyridone-5-carboxylic acid;1-Methyl-6-pyridone-3-carboxylic acid;1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic ac;1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid(SALTDATA: FREE);1-Methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid;Nudifloric Acid;1,2-dihydro-1-Methyl-2-ox...;1,2-dihydro-1-Methyl-2-oxopyridine-5-carboxylic acid
• CAS NO: 3719-45-7
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 3719-45-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 240-245°C
• Boiling Point: 329.6 °C at 760 mmHg
• Flash Point: 153.2 °C
• Appearance: /
• Density: 1.382 g/cm³
• Vapor Pressure: 3.44E-05mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, Methanol
• PKA: 3.85±0.50(Predicted)
• CAS DataBase Reference: 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid(3719-45-7)
• EPA Substance Registry System: 1-Methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid(3719-45-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3719-45-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A metabolite of Tryptophan-niacin.

InChI:InChI=1/C7H7NO3/c1-8-4-5(7(10)11)2-3-6(8)9/h2-4H,1H3,(H,10,11)

Synthetic route

methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (6375-89-9) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With water; sodium hydroxide In tetrahydrofuran at 35℃; for 3h;	99%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 3h;	80%
With water; sodium hydroxide In tetrahydrofuran at 20℃;	80%

1,6-dihydro-6-imino-1-methyl-3-pyridinecarboxamide (77837-12-8) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With potassium hydroxide for 4h; Heating;	90%

6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) + methyl iodide (74-88-4) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
Stage #1: 6-hydroxy-3-pyridinecarboxylic acid With sodium hydride In methanol at 20 - 60℃; for 0.583333h; Inert atmosphere; Stage #2: methyl iodide In methanol at 60℃; Stage #3: With hydrogenchloride; sodium hydroxide In methanol; water at 60℃;	69%
With potassium hydroxide In methanol; water for 12h; Reflux; Inert atmosphere;	63%
With alkali
With sodium methylate for 3h; Heating;

1-methylpyridinium-3-carb(ox)aldehyde (13441-42-4) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 1-methyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde (98279-50-6)

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III)	A n/a B 30%

3-(Carboxymethyl)-1-methylpyridiniumiodid → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 1-methyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde (98279-50-6) + 2-(1-methyl-6-oxo-1,6-d ihydropyridin-3-yl)acetic acid + 1,2-Dihydro-1-methyl-2-oxo-3-pyridinessigsaeure

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III) for 2h;	A 3% B 1.3% C 3.9% D 22%

3-(Carboxymethyl)-1-methylpyridiniumiodid → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III)	10%

nicotinic acid (59-67-6) + methanol (67-56-1) + dimethyl sulfate (77-78-1) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
Behandeln des Reaktionsprodukts mit K3 und wss. NaOH;

6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With potassium hydroxide durch Eindampfen und Erhitzen des Produkts mit Methyljodid und Methanol auf 100grad bis 110grad;
Multi-step reaction with 3 steps 1: sulfuric acid / 3 h / 65 - 70 °C 2: potassium carbonate / N,N-dimethyl-formamide / 72 h / 95 °C 3: sodium hydroxide; water / tetrahydrofuran / 3 h / 35 °C View Scheme

6-Chloro-3-pyridinecarboxylic acid (5326-23-8) + dimethyl sulfate (77-78-1) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
Erhitzen des Reaktionsgemisches mit wss. NaOH;

5-acetyl-1,2-dihydro-1-methyl-2(1H)-pyridone (1126-42-7) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With sodium hypobromide

methyl coumalate (6018-41-3) + methylamine (74-89-5) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With sodium hydroxide

methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (6375-89-9) → methanol (67-56-1) + 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With potassium chloride In water at 25℃; Rate constant;

3-carboxy-1-methyl-pyridinium-hydrogen sulfate → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III)

Trigonelline (535-83-1) + aqueous H2O2 + aq.-ethanolic NaOH → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Trigonelline (535-83-1) + potassium hexacyanoferrate(III) + aqueous NaOH → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

methyl iodide (74-88-4) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (6375-89-9)

Conditions	Yield
Stage #1: 6-hydroxy-3-pyridinecarboxylic acid With sodium hydride In methanol at 62℃; Stage #2: methyl iodide In methanol

N-methylnicotineamide iodide (6456-44-6) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / potassium permanganate, NH3(l) / 4 h / -33 °C 2: 90 percent / aq. KOH / 4 h / Heating View Scheme

3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (55676-25-0) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: anschliessendes Behandeln mit K3 2: water; hydrochloric acid 3: aqueous NaOBr View Scheme

1,2-dihydro-5-<(ethylenedioxy)-ethyl>-1-methyl-2(1H)-pyridone (162330-26-9) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydrochloric acid 2: aqueous NaOBr View Scheme

methyl 6-hydroxynicotinate (66171-50-4) → 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 72 h / 95 °C 2: sodium hydroxide; water / tetrahydrofuran / 3 h / 35 °C View Scheme

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + (1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphth[1,2-e]indol-10-ol → 5-((1S,3aR,5aS,6R,11bR,11cS)-14-(cyclopropylmethyl)-10-hydroxy-2,3,3a,4,5,6,7,11c-octahydro-1H-6,11b-(epiminoethano)-1,5a-methanonaphth[1,2-e]indole-3-carbonyl)-1-methylpyridine-2(1H)-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 1h;	75%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylamine (1172068-36-8) → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide (1196507-90-0)

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid; 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylamine With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 20℃; for 1h; Stage #2: With lithium hydroxide In dichloromethane for 0.5h;	69%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 3-chloro-N-((6-chloropyridin-3-yl)methyl)aniline → N-(5-((3-chlorophenylamino)methyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 5h; Inert atmosphere;	67%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 2-fluorophenylhydrazine (2368-80-1) → N’-(2-fluorophenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carbohydrazide

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-fluorophenylhydrazine With dmap In tetrahydrofuran at 20℃; for 2h;	65%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 4-methylthiosemicarbazide (6610-29-3) → 1-methyl-5-(4-methyl-5-sulfanyl-4H-1,2,4-triazol-3-yl)-1,2-dihydropyridin-2-one

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃;	65%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 0 - 20℃; Stage #2: With sodium hydroxide In ethyl acetate; N,N-dimethyl-formamide at 70℃;
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid; 4-methylthiosemicarbazide With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice; Stage #2: With sodium hydroxide In ethyl acetate; N,N-dimethyl-formamide at 70℃; for 0.666667h; pH=8 - 11; Inert atmosphere; Stage #3: With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide pH=5; Inert atmosphere;

styrene (100-42-5) + 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) → C22H19NO

Conditions	Yield
With dipotassium hydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In toluene at 160℃; for 24h; Molecular sieve; Inert atmosphere;	60%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-amine → N-(5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 0.2℃; for 2h;	55.3%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-((1,3-dihydroisobenzofuran-5-yl)methyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	55.3%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-(3-fluorobenzyl)-2-thiazolamine (884497-40-9) → N-(5-(3-fluorobenzyl)thiazol-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;	54.6%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h;	54.6%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-(4-(trifluoromethyl)benzyl)pyridin-2-amine → 1-methyl-6-oxo-N-(5-(4-(trifluoromethyl)benzyl)pyridin-2-yl)-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-(4-(trifluoromethyl)benzyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	50.5%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 0.5h; Inert atmosphere; Stage #2: 5-(4-(trifluoromethyl)benzyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	50.5%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 3-((6-aminopyridin-3-yl)methyl)benzonitrile → N-(5-(3-cyanobenzyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 85℃; for 1h; Stage #2: 3-((6-aminopyridin-3-yl)methyl)benzonitrile With pyridine In dichloromethane at 0 - 0.2℃; for 2h;	46%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 85℃; for 1h; Stage #2: 3-((6-aminopyridin-3-yl)methyl)benzonitrile With pyridine In dichloromethane at 0 - 20℃; for 2h;	46%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 1H-indazol-5-ylamine (19335-11-6) → N-(1H-Indazol-5-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃;	45%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + tert-butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (1318757-72-0) → N-[2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide (1318756-56-7)

Conditions	Yield
Stage #1: tert-butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate With hydrogenchloride In ethanol; water at 50℃; for 3h; Stage #2: With sodium hydrogencarbonate In ethanol; water Stage #3: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl acetamide at 0 - 60℃; for 6h;	44%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 4-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine (91477-84-8) → 1-methyl-5-(4-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5-carbonyl)pyridin-2(1H)-one

Conditions	Yield
Stage #1: 4-phenyl-4,5,6,7-tetrahydrothieno[3,2-c]-pyridine With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	43%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-[(3-fluorophenyl)methyl]pyridin-2-amine → N-(5-(3-fluorobenzyl)pyridin-2-yl)-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: 5-[(3-fluorophenyl)methyl]pyridin-2-amine In tetrahydrofuran at 20℃; for 4h;	41%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + cyclohexyl acrylate (3066-71-5) → cyclohexyl 2-(5-methyl-3,6-dioxo-1,3,5,6-tetrahydrofuro[3,4-c]pyridin-1-yl)acetate + cyclohexyl 2-(1-methyl-2,5-dioxo-1,2,5,7-tetrahydrofuro[3,4-b]pyridin-7-yl)acetate + dicyclohexyl 3,3'-(1-methyl-6-oxo-1,6-dihydropyridine-2,4-diyl)(2E,2'E)-diacrylate

Conditions	Yield
With dipotassium hydrogenphosphate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In toluene at 160℃; for 24h; Molecular sieve; Inert atmosphere;	A 10% B 5% C 40%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-(3-chloro-5-methoxybenzyl)pyridin-2-amine → N-(5-(3-chloro-5-methoxybenzyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; for 1h; Stage #2: 5-(3-chloro-5-methoxybenzyl)pyridin-2-amine With pyridine In dichloromethane at 0 - 20℃; for 2h;	38.6%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride at 80℃; Stage #2: 5-(3-chloro-5-methoxybenzyl)pyridin-2-amine In dichloromethane at 0 - 20℃; for 2h;	38.6%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-(4-fluorobenzyl)pyridin-2-amine → N-(5-(4-fluorobenzyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With pyridine; trichlorophosphate at 0 - 20℃;	38.4%
With pyridine; trichlorophosphate at 20℃;	38.4%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + N2-benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine → 5-[3-benzyl-5-(4-methyl-piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl]-1-methyl-1H-pyridin-2-one

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: N2-benzyl-6-(4-methyl-piperazin-1-yl)-pyridine-2,3-diamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #3: With acetic acid at 120℃; for 48h;	30%
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 1 h / 20 °C 2.1: acetic acid / 48 h / 120 °C View Scheme

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-(cyclohexylmethyl)pyridin-2-amine → N-(5-(cyclohexylmethyl)pyridin-2-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride In dichloromethane at 90℃; for 0.5h; Reflux; Stage #2: 5-(cyclohexylmethyl)pyridin-2-amine With pyridine In dichloromethane at 20℃; for 2h;	30%
Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With thionyl chloride In dichloromethane at 20 - 90℃; for 0.5h; Stage #2: 5-(cyclohexylmethyl)pyridin-2-amine With pyridine In dichloromethane	30%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 4-fluorophenyhydrazine hydrochloride (823-85-8) → 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid N'-(4-fluorophenyl)hydrazide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;	29%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 4-(3-fluorobenzyl)aniline → N-(4-(3-fluorobenzyl)phenyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With pyridine; trichlorophosphate at 20℃; for 1h;	27%
With pyridine; trichlorophosphate at 20℃; for 1h;	27%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 3-chloro-6-(3-chlorobenzyl)pyridazine → N-(6-(3-chlorobenzyl)pyridazin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 3h; Inert atmosphere;	26.9%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + (S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile hydrochloride (1448440-51-4) → (S)-N-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	21%

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 5-(3-fluorophenoxy)pyridin-2-amine → N-[5-(3-fluorophenoxy)pyridin-2-yl]-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU at 25℃; for 16h;	21%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 25℃; for 16h;	27.7 mg

1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (3719-45-7) + 4-(((3-ethoxy-4-isopropoxyphenyl)hydrazinocarbonylmethyl)amino)benzamidine dihydrochloride + trifluoroacetic acid (76-05-1) → 4-(1-(3-ethoxy-4-isopropoxyphenyl)-2-(N'-(1-methyl-6-oxo-1,6-dihydropyridine-3-carbonyl)hydrazino)-2-oxoethylamino)benzamidine trifluoroacetate (883574-25-2)

Conditions

Yield

Stage #1: 1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide at 0℃; Stage #2: 4-(((3-ethoxy-4-isopropoxyphenyl)hydrazinocarbonylmethyl)amino)benzamidine dihydrochloride With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 72h; Stage #3: trifluoroacetic acid In water; acetonitrile

20%

Upstream product

• 6375-89-9 methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate 
• 66171-50-4 methyl 6-hydroxynicotinate 
• 162330-26-9 1,2-dihydro-5-<(ethylenedioxy)-ethyl>-1-methyl-2(1H)-pyridone 
• 55676-25-0 3-(2-methyl-[1,3]dioxolan-2-yl)-pyridine 
• 6456-44-6 N-methylnicotineamide iodide 
• 535-83-1 Trigonelline 
• 77837-12-8 1,6-dihydro-6-imino-1-methyl-3-pyridinecarboxamide 
• 13441-42-4 1-methylpyridinium-3-carb(ox)aldehyde 
• 6018-41-3 methyl coumalate 
• 74-89-5 methylamine 
• 1126-42-7 5-acetyl-1,2-dihydro-1-methyl-2(1H)-pyridone 
• 5326-23-8 6-Chloro-3-pyridinecarboxylic acid 
• 77-78-1 dimethyl sulfate 
• 5006-66-6 6-hydroxy-3-pyridinecarboxylic acid 

Downstream Products

• 412035-58-6 1-methyl-5-nitro-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid 
• 10561-91-8 ethyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate 
• 73781-91-6 6-Chloronicotinic acid methyl ester 
• 701-44-0 1-methyl-2-pyridone-5-carboxamide 
• 5326-23-8 6-Chloro-3-pyridinecarboxylic acid 
• 677761-95-4 5-[(4S,5S)-4-(4-fluorophenyl)-4-(6-fluoropyridin-3-yl)-5-methyl-4,5-dihydro-1H-imidazol-2-yl]-1-methylpyridin-2(1H)-one 
• 1318756-56-7 N-[2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide 
• 883574-25-2 4-(1-(3-ethoxy-4-isopropoxyphenyl)-2-(N'-(1-methyl-6-oxo-1,6-dihydropyridine-3-carbonyl)hydrazino)-2-oxoethylamino)benzamidine trifluoroacetate 
• 1134916-90-7 5-[2-(2-chloro-5-fluoro-4-methoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one 
• 1134916-85-0 5-[2-(4-bromo-2-chloro-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one 

Relevant articles and documents

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COMPOUNDS AND USES THEREOF

The present invention features compounds useful in the treatment of neurological disorders and primary brain cancer. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders and primary brain cancer.

PYRIDINONES

The present invention encompasses compounds of general formula (I) wherein the groups R1 to R3 and X1 through X6 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.