Heterocyclic Building Blocks-Naphthyridine

As a common heterocyclic compound, it belong naphthyridine compound,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,100491-29-0,Molecular formula: C17H10ClF3N2O3,mainly used in chemical industry, its synthesis route is as follows.,100491-29-0

Example 7 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid. A mixture of tetrahydrofuran (450 cm3), water (50 cm3), methanesulfonic acid (127 cm3) and ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (United Kingdom Patent Publication No. GB 2,191,776) was heated at reflux for 1 hour, and then cooled to 25 C. The resulting crystals were isolated, washed with tetrahydrofuran, and dried under vacuum to afford 41.3 g (89%) of the above-titled compound: m.p.=250 C.; (Found: C, 50.4; H, 1.7; Cl, 9.9; F, 16.0; N, 8.0. C15 H6 ClF3 N2 O3 requires C, 50.8; H, 1.7; Cl, 10.0; F, 16.1; N, 7.9%); 1 H NMR (300 MHz, d6 -DMSO) delta 13.9 (s, 1H), 9.09 (s, 1H), 8.77 (d, J=7.5 Hz, 1H), 7.86 (td, J=5.9 and 8.8 Hz, 1H), 7.66 (ddd, J=2.7, 9.0 and 11.8 Hz, 1H), 7.39 (tm, J=8.6 Hz, 1H), 7.39 (tm, J=8.6 Hz, 1H); numax (DRIFTS) cm-1 3130, 3060, 2947, 2885, 2821, 2723, 2637, 2594, 1734, 1641, 1623, 1579, 1544, 1516.

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,belong naphthyridine compound

Reference£º
Patent; Pfizer Inc.; US6114531; (2000); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,100491-29-0,Molecular formula: C17H10ClF3N2O3,mainly used in chemical industry, its synthesis route is as follows.,100491-29-0

General procedure: Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) / carboxylic acid (2) (0.001 mol) and appropriate substituted benzazol-2-thiol derivative (0.001 mol) or N,N- dimethyl-(3-piperazin-1-yl)propan-1-amine (0.001 mol) and K2CO3 were dissolved in acetone (30 mL). The solution was refluxed at 40 C for 12 h. Reaction mixture was cooled down and adjusted to pH=7 by AcOH. Acetone was evaporated, the residue was washed with water, filtered, dried and recrystallized from EtOH.

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,belong naphthyridine compound

Reference£º
Article; Gencer, Huelya Karaca; Levent, Serkan; Acar Cevik, Ulviye; Oezkay, Yusuf; Ilg?n, Sinem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1162 – 1168;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,100491-29-0,Molecular formula: C17H10ClF3N2O3,mainly used in chemical industry, its synthesis route is as follows.,100491-29-0

a 1.91 g (5 mmol) 7-chlor-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid-ethylester is dissolved in 20 ml acetonitrile. 864 mg (6 mmol) 3-dimethylaminomethyl-3-hydroxy-pyrrolidine and 672 mg (6 mmol) 1,4-diazabicyclo[2.2.2]octane are added, and the mixture is stirred for 4 hours at room temperature. Thereafter 20 ml of water are added, and the pH is adjusted to 9 with deluted NaOH. The precipitate is isolated by filtration, washed with water and dried in vacuo. Yield: 1.66 g (68% of theory) 1-(2,4-difluorophenyl)-7-(3-dimethylaminomethyl-3-hydroxy-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid-ethylester, melting point 156-158 C.

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,belong naphthyridine compound

Reference£º
Patent; Bayer Aktiengesellschaft; US5173484; (1992); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,96568-07-9,Molecular formula: C14H12ClFN2O3,mainly used in chemical industry, its synthesis route is as follows.,96568-07-9

EXAMPLE 62 Ethyl 1-cyclopropyl-6-fluoro-7-[3-(1,2,3-triazol-1-yl]piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 3-(1,2,3-triazol-1-yl)piperidine (150 mg, 0.96 mmol) was added to a solution of ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.48 mmol) in a mixture of acetonitrile (10 ml) and pyridine (3 ml). The reaction mixture was heated at 100 C. for 6 hrs and then concentrated to dryness. The residue was diluted with water and thus solid separated was filtered, washed thoroughly with water and dried. Yield 90 mg, m.p. 205-206 C.; 1 H NMR (CDCl3) delta: 8.58 (s, 1H), 8.15 (d, 1H), 7.78 (s, 1H), 7.65 (s, 1H), 4.90 (m, 2H), 4.40 (m, 3H), 3.45 (m, 3H), 1.75-2.50 (m, 4H), 1.40 (t, 3H), 0.95-1.35 (m, 4H).

With the synthetic route has been constantly updated, we look forward to future research findings about Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,belong naphthyridine compound

Reference£º
Patent; SynPhar Laboratories, Inc.; US5342846; (1994); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

5,7-Dichloro-1,6-naphthyridine, cas is 337958-60-8, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Intermediate 16: 1,1-Dimethylethyl (3S)-3-{[(7-chloro-1,6-naphthyridin-5-yl)oxy]methyl}-3-fluoro-1-piperidinecarboxylate[0413]1,1-dimethylethyl (3S)-3-fluoro-3-(hydroxymethyl)-1-piperidinecarboxylate (1.406 g, 6.03 mmol) in DMF (20 ml) was added sodium hydride (0.313 g, 7.84 mmol) (60% dispersion in mineral oil). This was stirred for 15 min before adding 5,7-dichloro-1,6-naphthyridine (1.2 g, 6.03 mmol). This was warmed to room temp and stirred for 4 h. The reaction had gone to completion and so was cautiously quenched with aqueous ammonium chloride before partitioning between aqueous ammonium chloride and ethyl acetate. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine and concentrated in vacuo to give the crude product. This was dissolved in DCM and purified through silica (50 g), eluting with a gradient of 0-50% ethyl acetate in DCM. Appropriate fractions were concentrated in vacuo to yield the title compound as a cream foamy gum (1.91 g).[0415]LCMS: Rt=1.18 min, MH+=395.85

With the rapid development of chemical substances, we look forward to future research findings about 337958-60-8

Reference£º
Patent; GLAXO GROUP LIMITED; Atkinson, Francis Louis; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander George Steven; Wilson, David Matthew; US2013/40984; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.197507-59-8,1,6-Naphthyridine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Triethylamine (3.03 ml, 21.8 mmol), ethyl chloroformate (3.73 ml, 39.0 mmol) and 4-dimethylaminopyridine (DMAP) (2.40 g, 19.6 mmol) are added, at O0C, to a solution of l,6-naphthyridine-2-carboxylic acid (138) (Chan, L., Jin, H., Stefanac, T., Lavallee, J.F., Falardeau, G., Wang, W., Bedard, J., May, S. and Yuen, L., J. Med. Chem., 1999, 42, 3023-3025) (1.00 g, 5.75 mmol) in anhydrous dichloromethane (75 ml). After returning to ambient temperature, the reaction mixture is brought to reflux for 5 hours, the solution is evaporated to dryness and then the residue is purified on a column of alumina eluted with ethyl acetate to result in the ester 139 (517 mg, 2.56 mmol). Yield: 45%; Rf: 0.86 (Al2O3, ethyl acetate); melting point: 106-1080C; 1H NMR (400 MHz, CDCl3) d 1.41 (t, 3H, J = 7 Hz), 4.49 (q, 2H, J= 7 Hz), 8.02 (d, IH, J= 6 Hz), 8.21 (d, IH, J= 8.5 Hz), 8.39 (d, IH, J = 8.5 Hz), 8.75 (d, IH, J = 6 Hz), 9.29 (s, IH); 13C NMR (100 MHz, CDCl3) d 14.3, 62.0, 122.4, 122.7, 124.0, 137.2, 147.5, 149.7, 152.3, 152.9, 164.6; IR (KBr) V cm”1 : 1256, 1734; MS (m/z, %) 202 (M+, 3), 158 (18), 130 (100), 102 (15), 75 (22), 51 (16).

197507-59-8 1,6-Naphthyridine-2-carboxylic acid 735908, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); WO2008/12782; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Acetonitrile (100ml), 3-aminomethyl-4-methoxyiminopyrrolidine dimethanesulfonate (12. 5g), 2-chlorobenzaldehyde (lO. Og) and triethylamine (12.2g) were in turn introduced into a reaction vessel at room temperature. After stirring the mixture for about 0. 5h, 7- chloro-1-cyclopropyl-6-fluoro-1, 4-dihydro-4-oxo-1, 8- naphthyridine-3-carboxylic acid (10. Og) was introduced thereto. The resultant reaction mixture was stirred for about 15h at room temperature, cooled to 0~5&degC, and stirred for about 3h. The title compound in the form of solid was filtered, washed with acetonitrile, and dried to prepare 16.3g of the title compound (Yield: 90.0%). ‘H NMR (o, CDC13) : 8.74 (s, 1H), 8.66 (s, 1H), 7.96 (d, J=12. 4Hz, 1H), 7.84 (d, J=7. 3Hz, 1H), 7.29 (m, 2H), 7.16 (m, 1H), 4.59 (bs, 2H), 4.18 (m, 2H), 4.02 (m, 1H), 3.94 (s, 3H), 3.93 (m, 1H), 3.59 (m, 1H), 3.42 (m, 1H), 1.22 (m, 2H), 1.01 (m, 2H) Mass (FAB): 512 (M+H)

With the rapid development of chemical substances, we look forward to future research findings about 100361-18-0

Reference£º
Patent; LG LIFE SCIENCES LTD.; WO2003/87100; (2003); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

3-Bromo-1,5-naphthyridine, cas is 17965-71-8, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Example 2a: Synthesis of tert-butyl l,5-naphthyridin-3-ylcarbamate (D-12) C-2 D-12 [00315] To a solution of 3-bromo-l,5-naphthyridine (C-2) (4.181 g, 20.0 mmol, 1.0 eq ) in 1,4- dioxane (100 mL), tert-butylcarbamate (2.812 g, 24.0 mmol, 1.2 eq), cesium carbonate (9.132 g, 28.0 mmol, 1.4 eq), tris(benzylideneacetone)dipalladium (183 mg, 0.20 mmol, 0.01 eq) and Xantphos (347 mg, 0.60 mmol, 0.03 eq) were added. The mixture was heated at reflux for 16 h under an argon atmosphere. After the reaction mixture was cooled to RT, it was diluted with water (300 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (200 mL), dried over Na2S04 and filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (15 – 25% ethyl acetate- petroether) to afford the desired product, tert-butyl l,5-naphthyridin-3-ylcarbamate (D-12) (4.047 g, 82.5% yield) as a yellow oil. lR NMR (300 MHz, DMSO- 6) delta: 10.02 (bs, 1H), 8.94 (s, 1H), 8.87 (m, 1H), 8.47 (s, 1H), 8.28 (d, J = 8.4 Hz, 1H), 7.58 (m, 1H), 1.49 (s, 9H); ESI-MS m/z : 246.10 [M+H]+

With the rapid development of chemical substances, we look forward to future research findings about 17965-71-8

Reference£º
Patent; INTELLIKINE, LLC; REN, Pingda; LI, Liansheng; CHAN, Katrina; WO2013/78441; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

7-F4- (2-HVDROXVETHYLIDENE) PIPERIDIN-1-YLL-1-CVCLOPROPVL-6-FLUORO-4-OXO-1, 4- DIHVDRONAPHTHYRIDINE-3-CARBOXVIIC acid (163) A solution of amine 103 (256 mg, 1.06 MMOL) and triethylamine (0.5 mL, 3.55 MMOL) in ACETONITRILE (4 mL) was treated with 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1, 4-dihydro-naphthyridine-3- carboxylic acid (200 mg, 0.71 MMOL) under nitrogen and the reaction mixture was allowed to stir for 16 h. The resulting mixture was concentrated in vacuo, and the residue was washed with water (3 x 10 mL) and allowed to dry overnight to afford the title compound 163 (105 mg, 40%). MS 374 (M+H).

With the rapid development of chemical substances, we look forward to future research findings about 100361-18-0

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/33108; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, 8-Chloro-3-methoxy-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: (Method C1) Synthesis of N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine A 5 mL microwave tube was charged with 4-(4-(4-methoxyphenyl)phthalazin-1-ylamino)phenol and 3 equivalents of cesium carbonate (342 mg, 1.048 mmol) in 1.8 mL of DMF. The mixture was stirred at RT for 10 min. Following addition of 8-chloro-3-methoxy-1,5-naphthyridine (88 mg, 0.454 mmol), the vessel was capped and irradiated at 150 C. for 15 min in the microwave, at which time the reaction was determined complete by LC/MS. The mixture was cooled to ambient temperature and diluted with water. The solids were filtered and washed with water. The solids were triturated with methanol, filtered to remove remaining impurities, washed with additional methanol and dried under vacuum to afford N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-methoxyphenyl)phthalazin-1-amine as a light orange solid. MS [M+H]=502; Calc’d 501.54 for C30H25N5O3.

952059-69-7 8-Chloro-3-methoxy-1,5-naphthyridine 59427340, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem