Heterocyclic Building Blocks-Naphthyridine

23616-31-1, 1,6-Naphthyridin-5(6H)-one is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 3 8Bromo-1,6-naphthyridine-5(6H) -one (5) A suspension of 1.462 g (10 mmol) of 1,6-naphthyridine-5(6H)-one (3), 1.96 g (11 mmol) of N-bromosuccinimide, and 30 mL of dry dichlorothane is stirred at 25¡ã C. for 3.5 hours. The mixture is filtered, the solids are washed successively with small amounts of chloroform, water, and ether, then dried to leave 2.0 g of white solid, mp 245¡ã-250¡ã C. This is combined with 348 mg from an earlier run. The solids are triturated in 15 mL of hot water, collected by filtration, and dried to leave 2.28 g of pure product, mp 247¡ã-251¡ã C. A suspension of 360 mg of the product in methanol is treated with an excess of 2-propanoic hydrogen chloride, heated for 3 to 5 minutes, and stored at 25¡ã C. for 1.5 hours. The solids are collected by filtration, washed with 2-propanol, and dried to give 410 mg of yellow powder as the hydrochloride salt, mp >245¡ã C. (decomposition).

The synthetic route of 23616-31-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Warner-Lambert Company; US5391554; (1995); A;,
1,8-Naphthyridine – Wikipedia
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1,5-Naphthyridin-2(1H)-one, cas is 10261-82-2, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

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).

With the rapid development of chemical substances, we look forward to future research findings about 10261-82-2

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

1,5-Naphthyridine, cas is 254-79-5, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

To a stirred mixture of 1,5-naphthyridine (C-1) (50.0 g, 384 mmol, 1.0 eq) and sodium acetate(62.9 g, 768 mmol, 2.0 eq) in acetic acid (300 mL) at 80 C, a solution of bromine (67.5 g, 422 mmol, 1.1 eq) in acetic acid (80 mL) was added dropwise while keeping the reaction temperature at 80 C to 90 C. After stirring for 2 h at 80 C, the reaction was complete based on TLC analysis. The resulting mixture was cooled to RT and then filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (0-30% ethyl acetate-petroether) to afford the desired product 3-bromo-l,5-naphthyridine (C-2) (36.5 g, 45 % yield ) as a pale yellow solid. :H NMR (300 MHz, CDCl3-Patent; INTELLIKINE, INC.; REN, Pingda; LIU, Yi; LI, Liansheng; CHAN, Katrina; WILSON, Troy, Edward; CAMPBELL, Simon, Fraser; WO2011/149937; (2011); A1;,
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1,5-Naphthyridin-2(1H)-one, cas is 10261-82-2, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

To a suspension of Intermediate 3 (5.9 g) in dry DME (180 ml) and dry DMF (45 ml) at O0C under argon was added in portions NaH (60% w:w dispersion in mineral oil, 3.2 g). After stirring for 45 minutes, the mixture was treated with lithium bromide (8.8 g) and the suspension was allowed to warm to room temperature. After stirring for 45 minutes, the mixture was treated with allyl bromide (7 ml) and then stirred at 650C for 3 h. The mixture was cooled to room temperature and concentrated under reduced pressure, then t- BuOMe (300 ml) was added and the mixture was then washed with 1 N NH4CI (200 ml).The combined aqueous phases were extracted with f-BuOMe (2 x 100 ml). The organic phases were combined, washed with brine (200 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (4.29 g, 57%). To obtain an additional amount of the desired compound, the combined aqueous phases were extracted exhaustively with CH2CI2. Then, the organic extracts were combined, dried over MgSO4, filtered and evaporated under reduced pressure. Theresidue was purified by column chromatography on silica gel using a EtOAc and hexane gradient (50-75%) to give the desired product (1.5 g, 20%). [ES MS] m/z 187 (MH+).

With the rapid development of chemical substances, we look forward to future research findings about 10261-82-2

Reference£º
Patent; GLAXO GROUP LIMITED; ALEMPARTE-GALLARDO, Carlos; BARROS-AGUIRRE, David; CACHO-IZQUIERDO, Monica; FIANDOR-ROMAN, Jose Maria; LAVANDERA DIAZ, Jose Luis; REMUINAN-BLANCO, Modesto Jesus; WO2010/81874; (2010); A1;,
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91870-15-4, 2,5-Dichloro-1,8-naphthyridine is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The product from Example 21d (0.67 g, 3.36 mmol) and the product from Example9c (0.78 g, 3.36 mmol) in 10 mL ethanol were heated under reflux for 5.5 hr. The reaction mixture was cooled to room temperature and the solvent was removed concentrated under vacuum leaving yellow solid that was used without further purification (1.43 g, 100 percent).

The synthetic route of 91870-15-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; WO2008/133753; (2008); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,as a common compound, the synthetic route is as follows.

10g and 11.1gThe 1,5-naphthyridine derivative is dissolved in DMF.2.51 g of sodium hydride was added in portions on an ice bath.Add 5 minutes at room temperature after adding,After stirring for 2 hours at 50C,TLC showed that the raw material spots almost disappeared.Cool the reaction solution to ice bathIn an ice bath,Add 2.51g of sodium hydride,After stirring for 5 minutes,Add 4.5 ml acetyl chloride,There are a lot of white solids in the solution,After stirring for 3h at room temperature,Add 200ml of water to quench unreacted sodium hydride,Add 400ml of ethyl acetate to extractThe organic layer is washed three times,100ml each time.The organic layer is dry,concentrate,The concentrated oil was dissolved in 200 ml of THF.Join 37g TBAF,Stir at room temperature,The reaction gradually turned black.Stop the reaction after 30 minutes,Diluted the reaction with 100 ml of ethyl acetateWash 3 times,30ml each time.After the ethyl acetate layer is dry,concentrate,Get crude product.

The synthetic route of 952059-69-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,as a common compound, the synthetic route is as follows.

A 40% solution of tetrabutylammonium hydroxide in water (15 ml, 23 mmol) was added to a mixture of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (2.5 g, 8.8 mmol) and 4-amino-methyl-3-methoxyiminopyrrolidinium dimethanesulfonate (3.12 g, 9.3 mmol) in water (8 ml) at 20 – 25C and the mixture stirred for 24 hours. The resulting product was filtered and the cake washed with water (25 ml) followed by ethanol (25 ml) and dried under vacuum at 50C to give the title compound as a white solid (3.47 g). Characterising data were consistent with a standard sample of the title compound.

100361-18-0 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid 11055142, anaphthyridine compound, is more and more widely used in various.

Reference£º
Patent; LG Life Sciences, Ltd.; EP1214321; (2004); B1;,
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.

The synthetic route for diarylethene 1O is shown in Scheme 2 . The intermediate compounds 2 and 3 were synthesized according to the similar procedures as previous descriptions [57,58]. A mixture of compound 3 (0.56g, 1.0mmol), 4 (0.15g, 1.0mmol), EDCI (0.23g, 1.2mmol), HOBT (0.16g, 1.2mmol) and triethylamine (0.41mL, 3.0mmol) in anhydrous CH2Cl2 (50mL) was stirred at room temperature for 10h under a nitrogen atmosphere. The reaction mixture was washed with water, dried over anhydrous Na2SO4, and evaporated. The crude product was purified by column chromatography using petroleum ether/ ethyl acetate (v/v=1:1) as eluent to obtain 0.15g of the target compound 1O as white solid in 24% yield. M.p. 504-505K; 1H NMR (400MHz, THF, ppm): delta 1.82 (s, 3H), 1.89 (s, 3H), 2.32 (s, 3H), 6.71 (s, 1H), 7.27-7.30 (m, 1H), 7.46 (s, 1H), 7.67 (d, 2H, J=8.0Hz), 8.07 (d, 2H, J=8.0Hz), 8.12 (d, 1H, J=8.0Hz), 8.20 (d, 1H, J=8.0Hz), 8.52 (d, 1H, J=8.0Hz), 8.84 (s, 1H), 10.45 (s, 1H); 13C NMR (100MHz, THF, ppm): delta 11.50, 11.62, 12.01, 113.63, 118.49, 118.70, 122.10, 122.44, 122.73, 123.19, 124.37, 126.98, 131.74, 134.40, 134.77, 136.38, 136.93, 138.13, 139.25, 140.62, 151.42, 152.96, 153.39, 163.66; IR (KBr, nu, cm-1):712, 735, 759, 783, 809, 825, 843, 890, 937, 988, 1050, 1102, 1138, 1187, 1264, 1275, 1336, 1424, 1493, 1608, 1674, 2860, 2928, 3217, 3517; Anal. Calcd for C31H21F6N3OS2: C, 59.13; H, 3.36; N, 6.67; found: C, 59.04; H, 3.41; N, 6.59; HRMS-ESI (m/z): [M+Na+]+ calcd. 652.0928, found: 652.0901.

15992-83-3 1,8-Naphthyridin-2-amine 4173048, anaphthyridine compound, is more and more widely used in various.

Reference£º
Article; Zhang, Xiaoxia; Wang, Renjie; Fan, Congbin; Liu, Gang; Pu, Shouzhi; Dyes and Pigments; vol. 139; (2017); p. 208 – 217;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.100361-18-0,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,as a common compound, the synthetic 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).

As the paragraph descriping shows that 100361-18-0 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/33108; (2005); 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.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.

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.

The synthetic route of 100491-29-0 has been constantly updated, and we look forward to future research findings.

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
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