ethyl-3,1-(2,4-difluoroanilino)-2-(2,6-dichloro-5-fluoronicotinyl) acrylate
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 1h; Heating; | 86.5% |
With sodium hydride In 1,4-dioxane for 1h; Ambient temperature; | |
With sodium hydride In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux; | 8 g |
With sodium hydrogencarbonate In dichloromethane at 35℃; for 3h; Temperature; Solvent; Reagent/catalyst; |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
In diethyl ether; trichlorophosphate | 85% |
ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl]acetate
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With trichlorophosphate In diethyl ether; chloroform; water; N,N-dimethyl-formamide | 72.2% |
ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) Ac2O / 1.) 130 deg C, 1 h, 2.) CH2Cl2, RT, 0.5 h 2: 86.5 percent / NaH / tetrahydrofuran / 1 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: Ac2O / 15 h / 130 °C 2: ethanol / 1 h / Ambient temperature 3: NaH / dioxane / 1 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1.1: acetic anhydride / 1 h / 130 °C 1.2: 1 h 2.1: sodium hydride / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme |
2,6-dichloro-5-fluoro-3-nicotinoyl chloride
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) n-BuLi, biquinoline / 1.) THF, hexane, from -30 deg C to -5 deg C, 2.) THF, hexane, RT, 1 h 2: 1.) Ac2O / 1.) 130 deg C, 1 h, 2.) CH2Cl2, RT, 0.5 h 3: 86.5 percent / NaH / tetrahydrofuran / 1 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 2.) p-TsOH*H2O / 1.) ether, RT, 2 h, 2.) H2O, reflux, 2.5 h 2: Ac2O / 15 h / 130 °C 3: ethanol / 1 h / Ambient temperature 4: NaH / dioxane / 1 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1.1: 2,2'-biquinoline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -50 - 20 °C 2.1: acetic anhydride / 1 h / 130 °C 2.2: 1 h 3.1: sodium hydride / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme |
2,6-dichloro-5-fluoro-3-pyridinecarboxylic acid
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 2 h / 80 °C 2: 1.) n-BuLi, biquinoline / 1.) THF, hexane, from -30 deg C to -5 deg C, 2.) THF, hexane, RT, 1 h 3: 1.) Ac2O / 1.) 130 deg C, 1 h, 2.) CH2Cl2, RT, 0.5 h 4: 86.5 percent / NaH / tetrahydrofuran / 1 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: PCl5 / 0.13 h / 100 °C 2: 2.) p-TsOH*H2O / 1.) ether, RT, 2 h, 2.) H2O, reflux, 2.5 h 3: Ac2O / 15 h / 130 °C 4: ethanol / 1 h / Ambient temperature 5: NaH / dioxane / 1 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1.1: thionyl chloride / 2.5 h / 85 °C 2.1: 2,2'-biquinoline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -50 - 20 °C 3.1: acetic anhydride / 1 h / 130 °C 3.2: 1 h 4.1: sodium hydride / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme |
ethyl 2,6-dichloro-5-fluoropyridine-3-carboxylate
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 73.2 percent / trifluoroacetic acid, 7.5 N aq. HCl / 24 h / Heating 2: thionyl chloride / 2 h / 80 °C 3: 1.) n-BuLi, biquinoline / 1.) THF, hexane, from -30 deg C to -5 deg C, 2.) THF, hexane, RT, 1 h 4: 1.) Ac2O / 1.) 130 deg C, 1 h, 2.) CH2Cl2, RT, 0.5 h 5: 86.5 percent / NaH / tetrahydrofuran / 1 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid; hydrogenchloride / water / 26 h / Reflux 2.1: thionyl chloride / 2.5 h / 85 °C 3.1: 2,2'-biquinoline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -50 - 20 °C 4.1: acetic anhydride / 1 h / 130 °C 4.2: 1 h 5.1: sodium hydride / tetrahydrofuran / 1.5 h / Inert atmosphere; Reflux View Scheme |
2,4-difluorophenylamine
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanol / 1 h / Ambient temperature 2: NaH / dioxane / 1 h / Ambient temperature View Scheme |
2,6-dichloro-α-(ethoxymethylene)-5-fluoro-β-oxo-3-pyridinepropanoic acid ethyl ester
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanol / 1 h / Ambient temperature 2: NaH / dioxane / 1 h / Ambient temperature View Scheme |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate
7-([1α,5α,6α]-6-tert-Butoxycarbonylamino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid,ethyl ester
Conditions | Yield |
---|---|
With triethylamine In methanol for 1h; Substitution; Heating; | 99% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Conditions | Yield |
---|---|
In hydrogenchloride; water | 97.1% |
With methanesulfonic acid for 1h; Hydrolysis; Heating; | 89% |
With methanesulfonic acid In tetrahydrofuran; water | 41.3 g (89%) |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Ethyl (1α,5α,6α)-7-(6-nitro-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 82℃; for 6.5h; Substitution; | 89% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
5-chloro-1H-benzoimidazole-2-thiol
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 40℃; for 12h; | 88% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
2-Mercaptobenzothiazole
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 40℃; for 12h; | 86% |
(RS)-2-methylpiperazine
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
1-(2,4-Difluoro-phenyl)-6-fluoro-7-(3-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With pyridine for 3h; Ambient temperature; | 85.7% |
1-methyl-piperazine
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
1-(2,4-Difluoro-phenyl)-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With pyridine for 3h; Ambient temperature; | 85.3% |
1-Acetyl-1,2,3,6-tetrahydro-4-tributylstannyl-pyridine
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
ethyl 7-(1-acetyl-1,2,3,6-tetrahydro-4-pyridinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide for 7h; Heating; | 83% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
dimethyl-(3-piperazin-1-yl-propyl)-amine
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 40℃; for 12h; | 82% |
piperazine
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With pyridine for 3h; Ambient temperature; | 81.4% |
With pyridine at 20℃; for 24h; |
3-acetylaminopyrrolidine
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With pyridine for 3h; Ambient temperature; | 81.2% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
6,9-diazaspiro<4,5>decane dihydrochloride
ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(6,9-diazaspiro<4,5>decan-9-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene at 100℃; | 81% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
1α,5α,6β-6-dibenzylamino-3-azabicyclo[3.1.0]hexane
7-((1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 60℃; for 5h; | 80% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Benzimidazol-2-thiol
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 40℃; for 12h; | 80% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
5-methyl-1H-benzoimidazole-2-thiol
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 40℃; for 12h; | 79% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
(2S,4S)-4-Acetylamino-2-methylpyrrolidine
7-((2S,4S)-4-Acetylamino-2-methyl-pyrrolidin-1-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In pyridine at 65℃; for 336h; | 78% |
5-nitro-2-mercaptobenzimidazole
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 40℃; for 12h; | 78% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 20℃; for 0.166667h; | 77% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
72% | |
72% |
tert-butyl acetoacetate
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
7-(1-tert-Butoxycarbonyl-2-oxo-propyl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide for 20h; Ambient temperature; | 61% |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
4,7-diazaspiro<2,5>octane dihydrochloride
ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-(4,7-diazaspiro<2,5>octan-7-yl)-1,4-dihydro-4-oxo<1,8>naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene at 100℃; | 53% |
1,1-dimethylethyl-<3-(tri-n-butylstannyl)-2-cyclopenten-1-yl>carbamate
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
ethyl 1-(2,4-difluorophenyl)-7-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-1-cyclopenten-1-yl>-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 55h; Heating; | 42% |
(1R,4R)-2,5-diazabicyclo<2.2.1>heptane
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 70℃; for 1h; |
<1R,4R>-(1R-cis) 2,5-diazabicyclo<2.2.2>octane
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
Conditions | Yield |
---|---|
With triethylamine In pyridine at 40℃; for 48h; |
acetic anhydride
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
(3S)-3-azido-1-(phenylmethyl)pyrrolidine
B
7-((S)-3-Acetylamino-pyrrolidin-1-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate
(1R,4R,6S)-6-methyl-5-(phenylmethyl)2,5-diazabicyclo<2.2.1>heptane dihydrobromide
7-((1R,4R,6S)-5-Benzyl-6-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile |
The IUPAC name of Ethyl 1-(2,4-difluorophenyl)-7-chloro-6-fluoro-4-oxopyridino[2,3-b]pyridine-3-carboxylate is ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate. With the CAS registry number 100491-29-0, it is also named as 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester. It is almost white powder which should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.826; (4)ACD/LogD (pH 7.4): 1.826; (5)ACD/BCF (pH 5.5): 14.373; (6)ACD/BCF (pH 7.4): 14.373; (7)ACD/KOC (pH 5.5): 234.529; (8)ACD/KOC (pH 7.4): 234.529; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.589; (13)Molar Refractivity: 84.719 cm3; (14)Molar Volume: 251.215 cm3; (15)Polarizability: 33.585×10-24 cm3; (16)Surface Tension: 54.381 dyne/cm; (17)Enthalpy of Vaporization: 77.155 kJ/mol; (18)Vapour Pressure: 0 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Exact Mass: 382.033205; (21)MonoIsotopic Mass: 382.033205; (22)Topological Polar Surface Area: 59.5; (23)Heavy Atom Count: 26.
Preparation of Ethyl 1-(2,4-difluorophenyl)-7-chloro-6-fluoro-4-oxopyridino[2,3-b]pyridine-3-carboxylate: It can be obtained by 2-(2,6-dichloro-5-fluoro-pyridine-3-carbonyl)-3-(2,4-difluoro-phenylamino)-acrylic acid ethyl ester. This reaction needs reagent NaH and solvent dioxane at ambient temperature. The reaction time is 1 hours.
Uses of Ethyl 1-(2,4-difluorophenyl)-7-chloro-6-fluoro-4-oxopyridino[2,3-b]pyridine-3-carboxylate: It can react with piperazine to get 1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester. This reaction needs reagent pyridine at ambient temperature. The reaction time is 3 hours. The yield is 81.4%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:CCOC(=O)c1cn(c2c(c1=O)cc(c(n2)Cl)F)c3ccc(cc3F)F
2. InChI:InChI=1/C17H10ClF3N2O3/c1-2-26-17(25)10-7-23(13-4-3-8(19)5-11(13)20)16-9(14(10)24)6-12(21)15(18)22-16/h3-7H,2H2,1H3
3. InChIKey:JLSXYCZRMYCIMY-UHFFFAOYAK
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