Heterocyclic Building Blocks-Naphthyridine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.254-79-5,1,5-Naphthyridine,as a common compound, the synthetic route is as follows.

Example 12; 220 221 222Part A: To a solution of compound 220 (1.0Og, 6.02 mmol) in carbon tetrachloride (60 ml_) was added dropwise, bromine (1.15 g, 7.20 mmol) as a carbon tetrachloride solution (6 mL). The resulting solution was refluxed for 1 hour. Pyridine (0.5 ml_, 6.0 mmol) as a carbon tetrachloride solution (10 mL) was added over a period of 1 hour to the refluxing reaction mixture. The reaction was stirred at reflux for 16 hours at which time LC-MS indicated that the reaction was complete. The reaction mixture was cooled to room temperature, resulting in the formation of a precipitate, which was filtered. The carbon tetrachloride filtrate was set aside. The collected brown solid was taken up in 10% NaOH (100 mL) and stirred at room temperature for 1 hour. This solution was extratcted with chloroform. The chloroform and carbon tetrachloride solutions were combined and concentrated in vacuum. Purification by column chromatography (Sitheta2, 20% EtOAc / DCM) afforded compound 221 as a white solid 0.17 g, (14%). 1H NMR (400 MHz, DMSO-d6) delta 9.07 (d, 1 H), 9.02 (dd, 1 H), 8.74 (m, 1 H), 8.45 (m, 1 H), 7.83 (dd, 1 H).

254-79-5 1,5-Naphthyridine 136070, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; SCHERING CORPORATION; WO2008/82487; (2008); A2;,
1,8-Naphthyridine – Wikipedia
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254-79-5, 1,5-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Bromo-1,5-naphthyridine (5) To a stirring solutionof compound 4 (2.7 g, 20.76 mmol) and NaOAc(3.41 g,41.52 mmol) in 10 mL glacial AcOH at 85C was added a solution of Br2 (1 M) in AcOH (35 mL) for 5 h,then cooled to room temperature and concentrated in vacuum to remove AcOH.Purification by chromatography (PE/EA = 2:1) provided compound 5 (2.36 g, 55%) as a whitesolid. MP: 107~108C (Ref.2 108~109C).1H NMR (400 MHz,CDCl3): delta 8.96 (d, J = 2.1 Hz, 2H), 8.56 (s, 1H), 8.36 (d, J = 8.5 Hz, 1H), 7.69-7.56 (m, 1H).

254-79-5 1,5-Naphthyridine 136070, anaphthyridine compound, is more and more widely used in various.

Reference£º
Article; Wu, Jing-Fang; Liu, Ming-Ming; Huang, Shao-Xu; Wang, Yang; Bioorganic and Medicinal Chemistry Letters; vol. 25; 16; (2015); p. 3251 – 3255;,
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254-60-4, 1,8-Diazanaphthalene is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step D Preparation of 3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-N-Boc-propylamine (1-5) A solution of naphthyridine 1-4 (2.72 g) in methanol (20 mL) was hydrogenated in the presence of 5% rhodium on carbon (2.1 g; containing 63% of water) under 40 psi of hydrogen at 5 C. for 10 hours. The catalyst was filtered through Solka Flok and washed with methanol (25 mL twice). The filtrate and washings were combined, concentrated in vacuo, and dissolved in methanol (6.8 mL). To the solution was added water (6.8 mL) slowly at ambient temperature. The resulting solid was collected by filtration, washed with a mixture of water and methanol (2:1; 5 mL), and dried under vacuum to give the desired crystalline tetrahydronaphthyridine 1-5 (1.9 g). The mother liquor yielded an additional 5% of 1-5; m.p. 95.2-96.3 C. 1H NMR (400 MHz; CDCl3): delta 7.05 (d, J=7.4 Hz, 1H), 6.33 (d, J=7.3 Hz, 1H), 5.45 (bs, 1H), 4.92 (bs, 1H), 3.39 (m, 2H), 114 (s, 9H); J=7.3, 2H), 1.89 (m, 2H), 1.83 (m, 2H), 1.44 (s, 9H); 13C NMR (101 MHz; CDCl3): delta157.1, 156.0, 155.4, 136.7, 113.4, 111.3, 78.6, 41.4, 40.3, 35.0, 29.4, 28.4, 26.2, 21.3.

The synthetic route of 254-60-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck & Co., Inc.; US6423845; (2002); B1;,
1,8-Naphthyridine – Wikipedia
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254-60-4, 1,8-Diazanaphthalene is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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.

As the paragraph descriping shows that 254-60-4 is playing an increasingly important role.

Reference£º
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
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1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Int-19B. Ethyl (?)-4-(2-(l,8-naphthyridin-2-yl)vinyl)-lH-pyrrole-2-carboxylate: A solution of Int-19A (0.300 g, 2.08 mmol), commercially available ethyl 4-formyl-lH- pyrrole-2-carboxylate (0.348 g, 2.08 mmol), and 4-methylbenzenesulfonamide (0.356 g, 2.08 mmol) in toluene (4.5 mL) was stirred at reflux for 21 h. The precipitate was collected, triturated with DCM (2x) and the solid air-dried under vacuum to yield Int-19B (0.519 g, 94%) as a yellow solid. NMR (500 MHz, DMSO-c) delta 12.14 (br. s., 1H), (0504) 9.01 (dd, J = 4.3, 2.1 Hz, 1H), 8.41 – 8.28 (m, 2H), 7.82 (d, J = 16.2 Hz, 1H), 7.76 (d, J = 8.5 Hz, 1H), 7.52 (dd, J = 8.0, 4.1 Hz, 1H), 7.46 (s, 1H), 7.24 – 7.16 (m, 2H), 4.27 (q, J = (0505) 7.2 Hz, 2H), 1.31 (t, J= 7.0 Hz, 3H). HPLC retention time (Method 1): 1.973 mia; LCMS (ES): m/z 294.0 [M+H]+.

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (117 pag.)WO2018/89360; (2018); A1;,
1,8-Naphthyridine – Wikipedia
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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.

0003-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (30 mg), 1,3,4-thiadiazole-2-amine (25 mg) and potassium carbonate (17 mg) in dimethylsulfoxide (0.5 mL) was stirred at 150 C. for 30 minutes using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and water was added thereto. The solid matter was collected by filtration, thereby obtaining N-(7-bromo-1,5-naphthyridin-2-yl)-1,3,4-thiadiazole-2-amine.

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;,
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1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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.

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

Reference£º
Patent; PHARMACIA CORPORATION; WO2005/51904; (2005); 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.15992-83-3,1,8-Naphthyridin-2-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 20 The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (4.55 g), N,N’-carbonyldiimidazole (6.55 g) and 2-amino-1,8-naphthyridine (5.2 g). The product produced by precipitation in water (8.35 g; m.p. 85 C., viscous) is filtered and then dissolved in boiling 1-propanol (50 cc). After 1 hour’s cooling at 4 C., the crystallized solid is separated by filtration, washed with 1-propanol (2*5 cc) and dried at 35 C. under reduced pressure (0.067 kPa). N-(1,8-naphthyridin-2-yl)-4-methoxybenzamide (6.9 g) is produced, m.p. 150 C. 2-Amino-1,8-naphthyridine can be prepared according to U.S. Pat. No. 3,948,917.

The synthetic route of 15992-83-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Rhone-Poulenc Sante; US4642308; (1987); A;,
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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

To the compound 0001-1 (2.76 g), phosphorous oxychloride (8.3 mL) was added, and the mixture was stirred at 100C for 5 hours. The reaction solution which had been cooled to room temperature was added dropwise to a mixture of ethyl acetate (30 mL), water (30 mL), and sodium carbonate (9.57 g) in an ice-cooling bath over one hour. Further, water (10 mL) was added thereto, and sodium carbonate was added thereto until the pH reached 8.3. After stirring at room temperature for 10 minutes, the resulting mixture was subjected to liquid separation by the addition of ethyl acetate (270 mL) and water (200 mL). Further, the aqueous layer was extracted with ethyl acetate (200 mL) twice. The collected organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to obtain a compound 0001-2 (2.86 g) was obtained as a pale yellow solid. 1H-NMR (DMSO-d6) delta: 9.05 (1H, dd), 8.50 (1H, dd, J=8.9), 8.41 (1H, ddd), 7.87, (1H, d), 7.86 (1H, m).

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; FURUYA, Kentarou; TERAO, Takahiro; SEKINE, Shinichirou; NAKAGAWA, Daisuke; EP2727920; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1569-16-0, 2-Methyl[1,8]-Naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2-methyl-1,8-naphthyridine (6.024 g, 41.8 mmol) (from step 1) in anhydrous THF (140 mL) at -40 ¡ãC under nitrogen atmosphere was added a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (88.0 mL) and the reaction mixture was stirred at -40 ¡ãC for 30 min to give a blood-red solution. After stirring for 30 min at – 40 ¡ãC, neat diethyl carbonate (5.60 mL) was added drop wise to above solution in 5 min and the reaction mixture was warmed up to 0 ¡ãC (ice-bath) and stirred at that temperature for 2 h to give a dark reddish-orange solution. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (60.0 mL) to give an orange-red solution and the THF was removed in vacuo to give an orange-red mixture. The resulting mixture was extracted with ethyl acetate (3¡Á50 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4/MgSO4, filtered and evaporated in vacuo to afford a dark orange-red crystalline solid (8.65 g). The crude residue was purified by Silica-gel flash chromatography using a Varian SF-40-120 g Super Flash silica gel column and elution with 10-100percent ethyl acetate in n-heptane to afford the desired product as a yellow-orange crystalline solid (7.76 g, yield 85percent). LC-MS analysis of the solid shows the desired product’s mass: m/z 217 (M+H) and m/z 239 (M+Na); Calculated for C12H12N2O2: 216.23. 1H NMR (400 MHz, DMSO-d6): delta 1.21 (t, J = 7.0 Hz, 3H), 4.10 (q, 2H), 4.89 (s, 1H), 6.77 (d, J = 9.38 Hz, 1H), 7.14 (m, 1H), 7.46 (d, J = 9.36 Hz, 1H), 7.89 (d, 1H), 8.36 (d, 1H), 11.80 (brs, 1H, -OH). 1H NMR of the isolated product was superimposable with that of an authentic sample of the product.

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

Reference£º
Patent; SAINT LOUIS UNIVERSITY; INDALO THERAPUETICS, INC.; RUMINSKI, Peter, G.; GRIGGS, David, W.; SEIWERT, Scott; (155 pag.)WO2018/132268; (2018); A1;,
1,8-Naphthyridine – Wikipedia
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