Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.,100491-29-0

A. Method I: 560 mg (5mmol) of 1,4-diazabicyclo[2.2.2]octane and 890 mg (5.3 mmol) of 90% pure 4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindole are added to 1.9 g (5 mmol) of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate in 20 ml of acetonitrile. The mixture is stirred at room temperature for 3 hours and then concentrated in vacuo, and the residue is stirred with 80 ml of water. The undissolved residue is filtered off with suction, washed with water and dried. Yield: 1.6 g (64% of theory) of ethyl 1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-7-(4-methylamino-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-4-oxo-1,8-naphthyridine-3-carboxylate, melting point: 173-176 C. (with decomposition)

100491-29-0 Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 1268243, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; Bayer Aktiengesellschaft; US5464796; (1995); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

17965-71-8, 3-Bromo-1,5-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

17965-71-8, A mixture of 3-bromo-l,5-naphthyridine (300 mg, 1.44 mmol), BocNH2 (202 mg, 1.72 mmol), Pd2(dba)3 (66 mg, 0.072 mmol), XantPhos (125 mg, 0.215 mmol) and CS2CO3 (701 mg, 2.15 mmol) in anhydrous dioxane (8 mL) was degassed and purged with N2 for 3 times. Then the resulting reaction mixture was heated at 110 C for 16 h. The reaction mixture turned into yellow suspension from red. The reaction mixture was cooled to room temperature, then diluted with water (25 mL) and extracted with EtOAc (25 mL x3). The combined organic layer was filtered and the filtrate was washed with brine (25 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified by Combi Flash (25% to 60% EtOAc in pentane to give tert-butyl (l,5-naphthyridin-3-yl)carbamate (253 mg, yield: 72%) as a yellow solid. (0988) NMR (400 MHz, CDCb) d 1.57 (9H, s), 7.03 (1H, brs), 7.53 (1H, dd, J= 8.0, 4.0 Hz), 8.33 (1H, d , J= 8.4 Hz), 8.50 (1H, s), 8.90-9.00 (2H, m).

17965-71-8 3-Bromo-1,5-naphthyridine 12878818, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

10261-82-2, 1,5-Naphthyridin-2(1H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10261-82-2, 0001-2 Phosphorus oxychloride (8.3 mL) was added to 1,5-naphthyridin-2-ol (2.76 g), followed by stirring at 100 C. for 5 hours. The reaction mixture was cooled to room temperature, and added dropwise to a mixture of ethyl acetate (30 mL), water (30 mL), and sodium carbonate (9.57 g) over a period of 1 hour in an ice bath. Water (10 mL) was added thereto, and sodium carbonate was added thereto, followed by adjusting the pH of the resultant product to 8.3. The resultant product was stirred at room temperature for 10 minutes, and ethyl acetate (270 mL) and water (200 mL) were added thereto. The organic layer was collected by separation, and the aqueous layer was extracted two times with ethyl acetate (200 mL). The organic layer and the extraction liquid were combined, the resultant product was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 2-chloro-1,5-naphthyridine (2.86 g) as a pale yellow solid. MS m/z (M+H): 165.

The synthetic route of 10261-82-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

A stirred solution of 2-methyl-1,8-naphthyridine (57.5 g, 399 mmol) (available from Manchester Organics) and (R)-tert-butyl 3-(iodomethyl)pyrrolidine-1-carboxylate (124.2 g, 399mmcl) (Intermediate 1) in THF (1 L) was cooled to 0 ¡ãC and treated under nitrogen with a solution of lithium bis(trimethylsilyl)amide in THE (1M, 399 mL, 399 mmcl) over 20 mm and the reaction mixture was stirred at 0 ¡ãC for 3 h. The reaction was quenched with saturated ammonium chloride solution (500 mL) and water (500 mL) and ethyl acetate (1 L) was added. The layers were separated and the aqueous phase was extracted with further ethyl acetate (1 L). The combinedorganic layers were dried (MgSO4), filtered and evaporated in vacuo. The residual brown oil (162 g) was purified by chromatography on a silica cartridge (750 g) eluting with a gradient of 0 ? 100percent [ethyl acetate in (5percent MeOH ? 95percent ethyl acetate)] over 8 column volumes. The appropriate fractions were combined and evaporated in vacuo to give the title compound (46.65 g, 36percent) as an orange solid: LCMS (System A) RT=0.99 mm, 97percent, ES+ve m/z328 (M+H)?, [aiD2¡ã = + 22 (c 1.00in EtOH).

1569-16-0, 1569-16-0 2-Methyl[1,8]-Naphthyridine 74073, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; CAMPBELL, Ian Baxter; CAMPBELL-CRAWFORD, Matthew Howard James; HANCOCK, Ashley Paul; LEMMA, Seble; MACDONALD, Simon John Fawcett; PRITCHARD, John Martin; PROCOPIOU, Panayiotis Alexandrou; (64 pag.)WO2016/46230; (2016); 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.249889-68-7,8-Chloro-2-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,249889-68-7

2-Phenyl-[1,8]naphthyridin-3-ol (57 mg), 8-chloro-2-methoxy-[1,5]naphthyridine (50 mg), and 4-dimethylaminopyridine (94 mg) were suspended in 1,2-dichlorobenzene (1.5 ml), and the suspension was stirred at 130C for 8 hr. The reaction mixture was cooled to room temperature, and an aqueous sodium hydrogencarbonate solution was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (27 mg, yield 28%). 1H-NMR (CDCl3, 400 MHz): delta 3.68 (s, 3H), 7.15 (d, J = 9.0 Hz, 1H), 7.18 (d, J = 5.1 Hz, 1H), 7.40 – 7.42 (m, 3H), 7.46 (dd, J = 4.4, 8.3 Hz, 1H), 7.58 (s, 1H), 8.03 (dd, J = 2.0, 8.3 Hz, 1H), 8.32 (d, J = 9.3 Hz, 1H), 8.38 – 8.41 (m, 2H), 8.69 (d, J = 5.1 Hz, 1H), 9.10 (dd, J = 2.0, 4.1 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 403 (M+Na)+

As the paragraph descriping shows that 249889-68-7 is playing an increasingly important role.

Reference£º
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); 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.1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

0607-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (46 mg), 3-methyl-4-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propyl)morpholine (64 mg), sodium carbonate (40 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (7 mg), 1,4-dioxane (5 mL), and water (1 mL) was stirred at 80 C. for 5 hour in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-1H-pyrazol-1-yl)propyl)-3-methylmorpholine (77 mg). MS m/z (M+H): 372.

1309774-03-5, The synthetic route of 1309774-03-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); 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.1569-16-0,2-Methyl[1,8]-Naphthyridine,as a common compound, the synthetic route is as follows.

A solution of selenium dioxide (8.61 g, 77.56 mmol) in 1 ,4 dioxane (140 mL) with 0.5 mL of water was stirred at 100 ¡ãC for 5 min. The mixture was cooled down to 0 ¡ãC and 2-Methyl- 1 ,8-naphthyridine (7 g, 48.5 mmol) was added dropwise. The mixture was heated again at 100 ¡ãC for 5 h. Completion of the reaction was monitored by TLC. The reaction mixture was filtered through celite bed, washed with EtOAc (50 mL) and concentrated. The resulting crude mixture was dissolved in EtOAc (150 mL) and washed with water (3 x 60 mL), brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (brown solid). 1H NMR (300 MHz, DMSO-d6): delta 10.18 (s, 1 H), 9.28-9.27 (m, 1 H), 8.74 (d, J = 8.1 Hz, 1 H), 8.63 (d, J = 8.1 Hz, 1 H), 8.1 1 (dd, J = 8.4, 1.2 Hz, 1 H), 7.83-7.79 (m, 1 H). LCMS: (Method B) 159.0 (M +H), Rt. 2.44 min, 91.59percent (Max). HPLC: (Method B) Rt 2.41 min, 87.86percent (Max)., 1569-16-0

As the paragraph descriping shows that 1569-16-0 is playing an increasingly important role.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); 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.96568-07-9,Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,as a common compound, the synthetic route is as follows.,96568-07-9

EXAMPLE 52 Ethyl (1’RS,2’RS,6’RS)-1-cyclopropyl-7-(2′-ethyloxycarbonylaminomethyl-8′-azabicyclo[4.3.0]non-4′-en-8′-yl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate STR192 A mixture consisting of 828 mg (2.6 mmol) of ethyl 7-chloro -1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, 900 mg (4 mmol) of the product from Example K and 20 ml of acetonitrile is stirred at room temperature for three days. Subsequently, insoluble components are filtered off with suction and the solution is concentrated in vacuo. The crude product is purified by chromatography (eluent: dichloromethane/ methanol/conc. ammonia 15:4:0.5). Yield: 700 mg (56% of theory). 1 H-NMR (DMSO-d3): 8.36 (s, 1H, 2-H); 7.81 (d, 1H, 5-H); 7.21 (t, 1H, carbamate-NH); 5.73; 5.67 (2m, 2x 1H, HC=CH); 4.20; 3.99 (2q, 2x 2H, 2x ethyl-CH2); 3.86 (m, 1H); 3.78 (m, 1H); 3.56 (m, 2H); 3.13-3.01 (m, 2H); 2.89 (m, 1H); 2.35 (m, 1H); 2.18 (m, 2H); 1.88 (m, 2H); 1.26;-1.19 (2t, 2x 3H, 2x ethyl-CH3); 1.02; 0.88 ppm (2x H, 4x cyclopropyl-H).

96568-07-9 Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 0, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; Bayer Aktiengesellschaft; US5556979; (1996); A;,
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.7689-62-5,2-Chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

7689-62-5, A solution of the compound 0001-2 (2.88 g) and sodium acetate (2.89 g) in acetic acid (15 mL) was stirred at 85C for 5 minutes. A solution of bromine (0.99 mL) in acetic acid (2.5 mL) was dropwise added thereto. Further acetic acid (2 mL) was added dropwise thereto, and the mixture was stirred at 85C for 3 hours. To a 6 M aqueous sodium hydroxide solution (60 mL) under stirring with ice-cooling, the reaction solution which had been cooled to room temperature was added dropwise. The precipitated solid was separated by filtration, and the solid was then suspended in methanol (5 mL), and thereafter subjected to sonication. Thereafter, the suspension was filtered, and then the resulting solid was washed with methanol (3 mL). The obtained solid was suspended in a 75 v/v% aqueous methanol solution (8 mL), subjected to sonication, and then the suspension was filtered, and the residue was then washed with a 75 v/v% aqueous methanol solution twice to obtain a compound 0001-3 (3.33 g) as a pale yellow solid. 1H-NMR (DMSO-d6) delta: 9.13 (1H, d), 8.77 (1H, dd), 8.53 (1H, dd), 7.91 (1H, d). MS m/z (M+H): 245.

The synthetic route of 7689-62-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

959558-28-2, 4-Bromo-2,7-naphthyridin-1-amine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(1-Benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine23.7 g of tripotassium phosphate and 3.2 g of trans-dichlorobis(tricyclohexyl-phosphine)palladium(II) are added to a solution of 12.5 g of 4-bromo-2,7-naphthyridin-1-ylamine in 400 ml of diglyme and 15 ml of water. The mixture is heated to 125, and 25 g of 1-(benzenesulfonyl)-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine in 100 ml of diglyme are added dropwise over the course of 30 minutes. The mixture is stirred at 125 for 3 h, at room temperature for 20 h and the solvent is subsequently removed and the mixture is subjected to conventional work-up. The product is purified by means of flash chromatography over 330 g of silica with a methanol gradient in ethyl acetate with 200 ml/min with UV detection at 254 nm, giving a pure fraction (5.1 g) and a contaminated fraction (6.5 g) of 4-(1-benzenesulfonyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,7-naphthyridin-1-ylamine, M415.47 g/mol, M+H found 416., 959558-28-2

The synthetic route of 959558-28-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck Patent GmbH; Jonczyk, Alfred; Zenke, Frank T.; Amendt, Christiane; US2015/252041; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem