Heterocyclic Building Blocks-Naphthyridine

100491-29-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

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.

The chemical industry reduces the impact on the environment during synthesis,100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,I believe this compound will play a more active role in future production and life.

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

100361-18-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

The compound obtained from the preparation example 10 (4.44 g), 1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro[1,8] naphthyridine-3-carboxylic acid (3.45 g), and triethylamine (2.6 in,) were added to acetonitrile (50 ml) in order and the reaction mixture was sitirred at 4550 C. for 4 hr. The precipitate was filtered and dried to obtain the desired compound (5.31 g, 77.6%). [00102] 1H-NMR(CDCl3, ppm) 0.80 (3H, s), 1.07 (2H, bs), 1.17 (3H, s), 1.24 (5H, bs), 1.26 (2H, bs), 1.41 (9H, s), 3.40 (2H, bs), 3.553.60 (5H, m), 4.054.32 (4H, m), 5.07 (1H, bs), 8.03 (1H, d, J=12.4 Hz), 8.71 (1H, s); [alpha]D=+9.77 (c=1.19, CHCl3, 25.0 C.).

The chemical industry reduces the impact on the environment during synthesis,100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Dong Wha Pharm. Ind. Co., Ltd.; US6649763; (2003); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100361-18-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

Acetonitrile (1900ml), 3-aminomethyl-4-methoxyiminopyrrolidine dimethanesulfonate (248. Og) and water (100ml) were in turn introduced into a reaction vessel and cooled to 0- 5&deg C. Benzaldehyde (97.6g) and triethylamine (229. 1g) were in turn added to the reaction mixture. After stirring the mixture for 0. 5h, 7-chloro-1-cyclopropyl-6-fluoro-1, 4- dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acid (200. 0g) was introduced thereto. The resultant reaction mixture was slowly heated to room temperature, while stirring it. Then, the reaction was carried out by stirring the reaction mixture for about 3h at room temperature. The reaction material, which was formed in the form of a dispersion solution upon producing the title compound, was filtered, washed with water and acetonitrile, and then dried to prepare 320.3 g of the title compound (Yield: 94. 8%).’H NMR (6, CDC13) : 8.66 (s, 1H), 8. 32 (s, 1H), 7. 98 (d, J=12. 4Hz, 1H), 7.60 (d, J=7. 0Hz, 2H), 7. 37 (t, J=7.4Hz, 1H), 7.31 (t, J=7.4Hz, 2H), 4. 58 (s, 2H), 4. 21-4. 15 (m, 2H), 4.00 (m, 1H), 3.93 (s, 3H), 3.83 (m, 1H), 3.56 (m, 1H), 3.40 (m, 1H), 1.21 (m, 2H), 1.00 (m, 2H) Mass (FAB): 478 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, 100361-18-0

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

249889-68-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 8-chloro-2-(methyloxy)-l,5-naphthyridine (12 g, 61.7 mmol) in 4M HCl in dioxane (150 rtiL) was combined in a sealed tube and stirred at 100 0C for 20 h. The reaction was cooled to room temperature and then concentrated in vacuo. The residue was dried in a vacuum oven (80 0C) overnight to provide the bis- HCl salt of the title compound. MS(ES)+ m/e 181 [M+H]+. This crude product was used directly in the next step

The chemical industry reduces the impact on the environment during synthesis,249889-68-7,8-Chloro-2-methoxy-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/150827; (2008); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

7689-62-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2-Chloro-1,5-naphthyridine, cas is 7689-62-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 0.133 g, 0.472 mmol), 2-chloro-1,5-naphthyridine (0.100 g, 0.608 mmol) and DMSO (2 mL). N,N-Diisopropylethylamine (0.250 mL, 1.437 mmol) was added and the reaction mixture was sealed under argon and heated at 100 C. for 59 h. The reaction was cooled to room temperature and partitioned between water/DCM. The aqueous layer was extracted with DCM (3*) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco, (25 gram)) eluting with 2M NH3 in MeOH:CH2Cl2 (0:1?1:19) to give 67 mg (34%) of a white crystalline solid. ESI-MS 374.0 [M+1]. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.49 (dd, J=4.30, 1.56 Hz, 1H), 8.00 (d, J=3.33 Hz, 1H), 7.97 (d, J=3.33 Hz, 1H), 7.93 (d, J=9.19 Hz, 1H), 7.81-7.89 (m, 2H), 7.46 (dd, J=8.41, 4.11 Hz, 1H), 7.02 (d, J=9.19 Hz, 1H), 5.21 (m, 1H), 4.64-4.76 (m, 1H), 3.25-3.38 (m, 2H), 2.91-3.02 (m, 1H), 2.34-2.45 (m, 2H), 0.94-1.11 (m, 4H)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-Chloro-1,5-naphthyridine, 7689-62-5

Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1569-16-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-methyl-l,8-naphthyridine (2 g, 13.9 mmol) in ethanol (35mL) was added 10percent Pd/C, and the reaction mixture was stirred under H2 (10 psi) for 24 hours.Palladium was filtered out through celite and washed with excess ethanol. The filtrate wasconcentrated under vacuum to give 1.7 g (83percent) pink solid. NMR (CD3OD) 5 7.07 (d, 1H, J= 7.38 Hz), 6.32 (d, 1H, J = 7.25 Hz), 3.36-3.33 (m, 2H), 2.76-2.65 (m, 2H), 2.22 (s, 3H),25 1.87-1.82 (m, 2H). M+H=149.15.

The chemical industry reduces the impact on the environment during synthesis,1569-16-0,2-Methyl[1,8]-Naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; PHARMACIA CORPORATION; WO2005/51904; (2005); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

A solution of amine 135 (0.48 MMOL) and triethylamine (0.28 mL, 2.0 MMOL) in acetonitrile (7 mL) was treated with 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1, 4- DIHYDRO- [1, 8] naphthyridine-3-carboxylic acid (113 mg, 0.40 MMOL) under nitrogen. After 5 min, the reaction mixture was warmed to reflux temperature and the reaction mixture was allowed to stir for 24h. The resulting mixture was allowed to cool to room temperature, concentrated in vacuo and the residue was diluted with water. The product was collected by filtration, and then washed with water and a small amount of methanol to afford the title compound (178 mg, 87%) as a white solid. MS 511 (M+H).

100361-18-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,100361-18-0 ,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, other downstream synthetic routes, hurry up and to see

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

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Methyl[1,8]-Naphthyridine, and cas is 1569-16-0, its synthesis route is as follows.

To a mixture of 10percent palladium on carbon (0.369 g, 0.347 mmol) in MeOH (20 mL) under nitrogen in a 500 mL Parr reaction vessel was added 2-methyl-l,8-naphthyridine (0.500 g, 3.47 mmol). The reaction mixture was vacuum flushed with nitrogen (3x), then with hydrogen (3x) and vigorously shaken under hydrogen at 60 psi at -25 ¡ãC for 23 h. The reaction was filtered through a pad of Celite and thoroughly washed with MeOH. The filtrated was concentrated in vacuo to afford a mixture of the title compounds (506.1 mg) as a white solid. NMR indicated a mixture of two products in a ratio of 1 :0.18 which was used without further purification. LC-MS retention time = 1.70 min; m/z = (0434) 149.06 [M+H]+. (Column: Phenomenex Luna CI 8 50 x 2.0 mm 3 muiotaeta. Solvent A = 90percent Water : 10percent MeOH : 0.1percent TFA. Solvent B = 10percent Water : 90percent MeOH : 0.1percent TFA. Flow Rate = 0.8 mL/min. Start percent B = 0. Final percent B = 100. Gradient Time = 4 minutes, then a 1 minute hold at 100percent B. Oven temperature = 40 ¡ãC. Wavelength = 220 nm). Major product: NMR (400 MHz, DMSO-d6) delta 6.99 (d, J=7.3 Hz, 1H), 6.24 (d, J=7.0 Hz, 1H), 6.21 (br s, 1H), 3.26 – 3.19 (m, 2H), 2.59 (t, J=6.3 Hz, 2H), 2.16 (s, 3H), 1.74 (dt, J=l 1.7, 6.0 Hz, 2H). Minor product: NMR (400 MHz, DMSO-d6) delta 7.76 – 7.69 (m, 1H), 7.12 (d, J=7.0 Hz, 1H), 6.39 (dd, J=7.2, 4.9 Hz, 1H), 3.49 – 3.33 (m, 1H), 2.70 – 2.61 (m, 2H), 1.89 – 1.78 (m, 1H), 1.47 – 1.33 (m, 1H), 1.15 (d, J=6.3 Hz, 3H).

1569-16-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,1569-16-0 ,2-Methyl[1,8]-Naphthyridine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

254-60-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1,8-Diazanaphthalene, cas is 254-60-4,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A. A solution of [1,8]naphthyridine (0.2 mmol) and potassium amide (0.8 mmol) in liquid ammonia (20 mL) is stirred at -40 C. for 3 h. The solution is concentrated. Residue is partitioned between EtOAc and water. EtOAc layer is separated and washed successively with water and brine. EtOAc layer is dried over sodium sulfate, filtered and concentrated to give [1,8]naphthyridin-2-ylamine which is used as is for the next step.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1,8-Diazanaphthalene, 254-60-4

Reference£º
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

100491-29-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

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. Ethyl 7-((benzo[d]thiazol-2-yl)thio)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (3) Yield: 86 %, M.P. = 184.7 C. HPLC: 99.6 % purity. FTIR (ATR, cm-1 ): 1736 (C=O, ester), 1624 (C=O, ketone), 1043, 806, 750. 1H-NMR (300 MHz, DMSO-d6): delta = 1.25 (3H, t, J= 7.05 Hz , -CH3), 4.22 (2H, q, J= 7.05 Hz , -CH2-), 6.96-7.08 (2H, m, phenyl H(3), H(5)), 7.54-7.59 (2H, m, benzothiazole H(5), H(6)), 7.60-7.69 (1H, m, phenyl H(6)), 7.96-8.00 (1H, s, benzothiazole H(4), H(7)), 8.40 (1H, d, J= 8.85 Hz, naphthyridine H(5)), 8.64 (1H, s, naphthyridine H(2).13C-NMR (75 MHz, DMSO-d6): delta = 14.60, 60.81, 105.14 (q, J= 23.5 Hz), 112.49 (d, J= 22.6 Hz), 113.04, 121.01 (d, J= 19.1 Hz), 121.77 (d, J= 2.9 Hz), 122.04, 123.26, 124.28 (d, J= 13.3 Hz), 126.65, 127.14, 131.69 (d, J= 10.3 Hz), 137.28, 146.16, 149.15 (d, J= 21.0 Hz), 149.62, 152.03, 152.98 (d, J= 253.5 Hz), 155.09 (d, J= 3.4 Hz), 157.97 (dd, J= 250.7 Hz- 13.4 Hz), 162.77 (dd, J= 248.1 Hz- 11.6 Hz), 163.80, 173.15. HRMS (m/z): [M+H]+ calcd for C24H14N3O3S2F3: 514.0501; found 514.0492.

The chemical industry reduces the impact on the environment during synthesis,100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,I believe this compound will play a more active role in future production and life.

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