Category: 249889-68-7

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.

The residue was suspended in diisopropylethylamine (7 ml), phosphorus oxychloride (1.5 ml) was added to the suspension, and the mixture was stirred at 100C for one hr. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give 8-chloro-2-methoxy-[1,5]naphthyridine (572 mg, yield 29%) (3 steps). 8-Chloro-2-methoxy-[1,5]naphthyridine (50 mg), 5,6-dimethyl-[2,2′]bipyridinyl-3-ol (51 mg), and 4-dimethylaminopyridine (94 mg) were dissolved in dimethylsulfoxide (1.5 ml), cesium carbonate (251 mg) was added to the solution, and the mixture was stirred at 130C overnight. The reaction mixture was cooled to room temperature, and water was added thereto. 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 (70 mg, yield 75%). 1H-NMR (CDCl3, 400 MHz): delta 2.34 (s, 3H), 2.66 (s, 3H), 3.92 (s, 3H), 6.92 (d, J = 5.4 Hz, 1H), 7.17 – 7.26 (m, 3H), 7.65 (dd, J = 7.6, 7.6 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 8.36 (s, 1H), 8.53 (d, J = 5.9 Hz, 1H), 8.58 (m, 1H) Mass spectrometric value (ESI-MS, m/z): 381 (M+Na)+

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; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

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, 249889-68-7

With the rapid development of chemical substances, we look forward to future research findings about 8-Chloro-2-methoxy-1,5-naphthyridine

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

8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Example 13; iV-(l-ethyl-lJ-pyrazol-4-yl)-2-[2-methoxy-4-(6-methoxy-l,5-naphthyridin- 4~yloxy)phenyl] acetamide; A mixture of 4-chloro-6-methoxy-l,5-naphthyridine (0.08 g), JV-(I -ethyl-lH-pyrazol-4- yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide (0.113 g), 4-dimethylaminopyridine (0.151 g) and chlorobenzene (1 ml) was stirred and heated under argon to 140C for 14 hours. The resultant mixture was cooled to ambient temperature and partitioned between methylene chloride and 2N aqueous hydrochloric acid. The organic extract was dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a solvent gradient from ethyl acetate to a 19:1 mixture of ethyl acetate and methanol as eluent. There was thus obtained the title compound as a solid (0.018 g); 1H NMR Spectrum:5 (DMSOd6) 1.32 (t, 3H), 3.58 (s, 2H), 3.75 (s, 3H), 3.95 (s, 3H), 4.07 (q, 2H), 6.79 (m, IH), 6.91 (d, IH), 6.93 (d, IH), 7.29 (d, IH), 7.31 (d, IH), 7.41 (s, IH), 7.87 (s, IH), 8.28 (d, IH), 8.61 (d, IH), 10.01 (s, IH); Mass Spectrum: M+H+ 434., 249889-68-7

With the rapid development of chemical substances, we look forward to future research findings about 8-Chloro-2-methoxy-1,5-naphthyridine

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113548; (2007); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

8-Chloro-2-methoxy-1,5-naphthyridine, cas is 249889-68-7, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

A mixture of 8-chloro-2-methoxy-l,5-naphthyridine (31.83 mg, 163.56 umol, 2.00 eq), 6-[4-(4-methylpiperazin-l-yl)-l-piperidyl]-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrazolo[l,5-a]pyrimidine (74.19 mg, 81.78 umol, 1.00 eq), Pd(dppf)Cl2 (11.97 mg, 16.36 umol, 0.20 eq), K2CO3 (33.91 mg, 245.34 umol, 3.00 eq) in dioxane/H20 (6.00 mL/0.9 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 120C for 1 hour under N2 atmosphere until LCMS showed the starting material was consumed completely. The reaction mixture was concentrated in vacuo to give a residue, which was purified by Biotage flash reversed-phase C-18 column chromatography eluting with MeOH/H20 (MeOH in water from 10% to 100%) to give the product of 2-methoxy-8-[6-[4-(4-methylpiperazin-l- yl)-l-piperidyl]pyrazolo[l,5-a]pyrimidin-3-yl]-l,5-naphthyridine (60) as a yellow solid. LC/MS (method 3): fe = 2.22 min, mlz (M + H)+ = 459.2; NMR (400 MHz, MeOD) delta 9.50 (s, 1H), 8.88 (d, J= 5.2 Hz, 1H), 8.77 (d, J= 2.4 Hz, 1H), 8.67 (d, J = 4.8 Hz, 1H), 8.41 (d, J = 2.8 Hz, 1H), 8.19 (d, J = 9.2 Hz, 1H), 7.24 (d, J = 9.2 Hz, 1H), 4.15 (s, 3H), 3.77-3.74 (m, 2H), 2.82-2.40 (m, 11H), 2.30 (s, 3H), 2.10-2.07 (m, 2H), 1.80-1.69 (m, 2H).

249889-68-7, As the rapid development of chemical substances, we look forward to future research findings about 249889-68-7

Reference£º
Patent; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; YU, Paul, B.; HUANG, Wenwei; SANDERSON, Philip, Edward; JIANG, Jian-kang; SHAMIM, Khalida; ZHENG, Wei; HUANG, Xiuli; TAWA, Gregory; LEE, Arthur; ALIMARDANOV, Asaf; HUANG, Junfeng; (357 pag.)WO2018/200855; (2018); 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., Author tianliPosted on September 25, 2020Categories 249889-68-7, naphthyridineTags M.W:100-200

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

Example 81 : (S)-3-(2,3-dihydro-benzo [ 1 ,4] dioxin-6-yl)-5- { [2-(6-methoxy- [l,5]naphthyridin-4-ylamino)-ethylamino]-methyl}-oxazolidin-2-one:; 81. i. N1 -(6-methoxy-fl, 5]naphthyridin-4-yl)-ethane-l,2-diamine:; A mixture of 8-chloro-2-methoxy-l,5-naphthyridine (1.71 g, 8.81 mmol) and ethylenediamine (1.18 mL, 2 eq.) was heated slowly to 800C over 1 h and subsequently up to 1000C for 2 h. After cooling to rt, the yellow solution was taken in DCM and successively washed with NaHCO3. The aq. layer was back extracted with DCM (3 times) and the combined org. layers were concentrated to afford the title intermediate as a pale yellow oil (0.98 g, 51% yield). MS (ESI, m/z): 219.4 [M+H+].

249889-68-7 8-Chloro-2-methoxy-1,5-naphthyridine 22244395, anaphthyridine compound, is more and more widely used in various fields.

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/126024; (2008); A2;,
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.

A mixture of 8-chloro-2-methoxy-l,5-naphthyridine (31.83 mg, 163.56 umol, 2.00 eq), 6-[4-(4-methylpiperazin-l-yl)-l-piperidyl]-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrazolo[l,5-a]pyrimidine (74.19 mg, 81.78 umol, 1.00 eq), Pd(dppf)Cl2 (11.97 mg, 16.36 umol, 0.20 eq), K2CO3 (33.91 mg, 245.34 umol, 3.00 eq) in dioxane/H20 (6.00 mL/0.9 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 120C for 1 hour under N2 atmosphere until LCMS showed the starting material was consumed completely. The reaction mixture was concentrated in vacuo to give a residue, which was purified by Biotage flash reversed-phase C-18 column chromatography eluting with MeOH/H20 (MeOH in water from 10% to 100%) to give the product of 2-methoxy-8-[6-[4-(4-methylpiperazin-l- yl)-l-piperidyl]pyrazolo[l,5-a]pyrimidin-3-yl]-l,5-naphthyridine (60) as a yellow solid. LC/MS (method 3): fe = 2.22 min, mlz (M + H)+ = 459.2; NMR (400 MHz, MeOD) delta 9.50 (s, 1H), 8.88 (d, J= 5.2 Hz, 1H), 8.77 (d, J= 2.4 Hz, 1H), 8.67 (d, J = 4.8 Hz, 1H), 8.41 (d, J = 2.8 Hz, 1H), 8.19 (d, J = 9.2 Hz, 1H), 7.24 (d, J = 9.2 Hz, 1H), 4.15 (s, 3H), 3.77-3.74 (m, 2H), 2.82-2.40 (m, 11H), 2.30 (s, 3H), 2.10-2.07 (m, 2H), 1.80-1.69 (m, 2H).

249889-68-7, The synthetic route of 249889-68-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; YU, Paul, B.; HUANG, Wenwei; SANDERSON, Philip, Edward; JIANG, Jian-kang; SHAMIM, Khalida; ZHENG, Wei; HUANG, Xiuli; TAWA, Gregory; LEE, Arthur; ALIMARDANOV, Asaf; HUANG, Junfeng; (357 pag.)WO2018/200855; (2018); 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