Category: naphthyridine

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,1569-16-0

In the second step, 2-methyl-1,8-naphthyridine (27 mmol, 3.8 g) was dissolved in diethyl ether (50 mL) under a nitrogen atmosphere, and then cooled to -78¡ã C., and added dropwise with stirring (0.5 h increments). (b) Diethyl ether solution (20mL) of CH3-Li (32mmol, 1.6M, purchased from JV of BAHL Technology, Inc.), and then warmed to room temperature (25¡ãC) and stirred for 12h. The reaction was quenched by adding 15mL of saturated aqueous ammonium chloride. The organic layer was separated and the aqueous layer was extracted with chloroform three times. The organic layers were combined and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give an orange-red oil. KMnO4 (96 mmol, 15.2 g, purchased from Beijing Chemical Industry Plant) was added at room temperature. After stirring for 6 h at 25¡ã C., the mixture was suction filtered, and the filtrate was evaporated under reduced pressure to obtain a crude solid product, which was further purified by column chromatography (petroleum ether/ethyl acetate mixture with a volume ratio of 100/1). A compound (known compound) having the structure represented by the formula (1-1) is obtained,The yield was 75percent.

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

Reference£º
Patent; Chinese Academy Of Sciences Chemical Institute; Fan Qinghua; Ma Wenpeng; Chen Fei; He Yanmei; (51 pag.)CN105111208; (2018); B;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1,8-Diazanaphthalene, cas is 254-60-4, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

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., 254-60-4

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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

Name is 6-Bromo-1,8-naphthyridin-2-ol, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 72754-05-3, its synthesis route is as follows.,72754-05-3

A mixture of 6-bromo-lH-l, 8-naphthyridin-2-one (1 equiv, which was prepared as per prepared as per- 1.3), Pd (PPh3)2Cl2 (0.1 equiv), Cul (0.15 equiv), (i-Pr)2EtN (4 equiv) in DMF (15 times) was deoxygenated with nitrogen for 15 minutes. Then vinyl trimethyl silane (2 equiv) was added and heated to 125C for lOh. The reaction was monitored by thin layer chromatography. Filtered through a pad of silica gel at room temperature. The filtrate was concentrated and the residue was purified by silica gel chromatography (eluted with 20 to 30% ethyl acetate/hexane) to provide the title compound as a solid (30% yield). ESI MS m/z -245.22(M+H)+.

With the complex challenges of chemical substances, we look forward to future research findings about 6-Bromo-1,8-naphthyridin-2-ol

Reference£º
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; GAMPA, Venugopala Krishna; GANGANAMONI, Srinivasulu; SIRIGIREDDY, Balakrishna Reddy; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2015/186137; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, and cas is 100491-29-0, its synthesis route is as follows.,100491-29-0

A. Ethyl 7-([S,S]-2,8-diazabicyclo[4.3.0]non-8-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 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 are stirred with 680 mg (5.4 mmol) of [S,S]-2,8-diazabicyclo[4.3.0]nonane at 10 C. for 3 hours in 20 ml of acetonitrile and in the presence of 560 mg (5 mmol) of 1,4-diazabicyclo[2.2.2]octane. The suspension is filtered with suction, washed with water and dried. 0.35 g of product is obtained. By concentrating the mother liquors, stirring the residue with water, isolating the undissolved product and purifying by chromatography (silica gel, eluent: dichloromethane/methanol/17% strength aqueous ammonia), a further 0.7 g of product is isolated. Total yield: 1.05 g (44% of theory), Melting point: 184-185 C. (with decomposition), [alpha]D23: +6.8 (c=0.46, CHCl3)

With the complex challenges of chemical substances, we look forward to future research findings about 100491-29-0,belong naphthyridine compound

Reference£º
Patent; Bayer Aktiengesellschaft; US5480879; (1996); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 8-Chloro-3-methoxy-1,5-naphthyridine, and cas is 952059-69-7, its synthesis route is as follows.,952059-69-7

Step 1: N-(5-(7-Methoxyquinolin-4-ylamino)pyrimidin-2-yl)benzamide In a screw cap test tube were dissolved 8-chloro-3-methoxy-1,5-naphthyridine (281 mg, 1443 mumol), N-(5-aminopyrimidin-2-yl)benzamide (281 mg, 1312 mumol) and pyridinium p-toluenesulfonate (494 mg, 1968 mumol) in butan-2-ol (2623 mul, 1312 mumol) then heated at 100 C. The reaction turned black in a minute. After 1 h, the reaction mixture showed full conversion to product according to LCMS. The reaction mixture was diluted with CH2Cl2, neutralized with sat. NaHCO3. An emulsion was formed but the two layers eventually separated. The aqueous phase was extracted 3 times with CH2Cl2, washed with brine, dried over MgSO4, filtered and evaporated under reduce pressure to give a tan solid. The solid was triturated with hexane, filtered, and dried under vacuo. Brown solid was collected. LCMS confirmed the presence of the product, N-(5-(7-methoxy-1,5-naphthyridin-4-ylamino)pyrimidin-2-yl)benzamide. MS Calcd for C20H16N6O2: [M]+=372. Found: [M+H]+=373.

With the complex challenges of chemical substances, we look forward to future research findings about 952059-69-7,belong naphthyridine compound

Reference£º
Patent; CEE, Victor J.; DEAK, Holly L.; DU, Bingfan; GEUNS-MEYER, Stephanie D.; HUA, Zihao; MARTIN, Matthew W.; MARX, Isaac; NGUYEN, Hanh Nho; OLIVIERI, Philip R.; PANTER FABER, Kathleen; ROMERO, Karina; SCHENKEL, Laurie; WHITE, Ryan; US2014/336182; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,7-Bromo-2-chloro-1,5-naphthyridine,1309774-03-5,Molecular formula: C8H4BrClN2,mainly used in chemical industry, its synthesis route is as follows.,1309774-03-5

0387-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (100 mg), pyrimidine-5-amine (38 mg), tris(dibenzylideneacetone)dipalladium(0) (37 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (47 mg), cesium carbonate (267 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 6 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the obtained solution was purified by silica gel column chromatography (methanol-ethyl acetate), thereby obtaining 6-chloro-N-(pyrimidin-5-yl)-1,5-naphthyridine-3-amine (32 mg). MS m/z (M+H): 258.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine,belong naphthyridine compound

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

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 3-Bromo-1,5-naphthyridine, and cas is 17965-71-8, its synthesis route is as follows.,17965-71-8

General procedure: To a solution of aryl bromide (0.3mmol) in anhydrous 1,4-dioxane (10mL) was added boronic acid (0.45mmol) and a solution of K3PO4 (130mg, 0.61mmol) in water (2mL). The mixture was purged with nitrogen gas for 5min. Pd(dppf)Cl2.CH2Cl2 (12mg, 0.015mmol) was added and the mixture was heated at 100C. After 5h, the reaction mixture was cooled to room temperature, filtered through celite and washed with ethyl acetate. The filtrate was washed with water (50mL), brine (50mL), dried (anhydrous Na2SO4) and concentrated under reduced pressure. The residue was purified by preparative HPLC (C18 column, 20:80 acetonitrile/water with 0.1% formic acid). Compound containing fractions were lyophilized to afford the product. 5.1.2 1-(5-(1,5-Naphthyridin-3-yl)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-2-yl)-3-ethylurea (6) (0026) Synthesized from 4 and 5 following the general procedure for Suzuki coupling in 58% yield as a pale yellow solid. 1H NMR (400MHz, DMSO-d6) delta 9.52 (s, 1H), 9.05-9.04 (m, 1H), 8.82-8.81 (m, 1H), 8.50-8.46 (m, 4H), 8.26 (s, 1H), 7.85-7.82 (m, 1H), 7.62-7.59 (m, 1H), 3.27-3.19 (m, 2H), 1.12 (t, 3H, J=7.2Hz); 13C NMR (100MHz, DMSO-d6) delta 165.7, 153.7, 153.5, 151.6, 151.3, 149.1, 142.8, 142.4, 142.2, 142.0, 141.8, 138.7, 136.4, 136.1, 132.7, 125.7, 125.6, 124.5, 123.6, 120.9, 118.3, 115.6, 109.6, 33.4, 14.7. MS (ESI) m/z 445.1 (M+H)+; HRMS: calcd for C20H15F3N6OS (M+H)+, 445.1053; found, 445.1046. mp: 232.4-232.7C.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Bromo-1,5-naphthyridine

Reference£º
Article; Ho, Soo Yei; Wang, Weiling; Ng, Fui Mee; Wong, Yun Xuan; Poh, Zhi Ying; Tan, Sum Wai Eldwin; Ang, Shi Hua; Liew, Si Si; Joyner Wong, Yin Sze; Tan, Yvonne; Poulsen, Anders; Pendharkar, Vishal; Sangthongpitag, Kanda; Manchester, John; Basarab, Gregory; Hill, Jeffrey; Keller, Thomas H.; Cherian, Joseph; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 610 – 621;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 8-Chloro-3-methoxy-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 952059-69-7, its synthesis route is as follows.,952059-69-7

Example 103; 2-(2-(7-Methoxy-l,5-naphthyridin-4-ylamino)ethyl)-6-(4-methylthiophen-2- yl)pyridazin-3(2H)-one. A suspension of 2-(2-aminoethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (360 mg, 1530 mumol) and 8-chloro-3-methoxy-l,5-naphthyridine (298 mg, 1530 mumol) in iPrOH (5 mL) was heated to 100 C in a sealed vial. After 3 h, the reaction mixture was partitioned between CH2Cl2 (30 mL) and IM NaOH (10 mL). The organic layer was dried over MgSO4, concentrated to a solid, and purified on 40 gram of silica eluting with 0-60% of 6% (2M NH3 in MeOH)/ CH2Cl2. The resulting oil was crystalized from ACN (0.5 mL). MS (ESI pos. ion) m/z (MH+): 394. Calc’d exact mass for C20Hi9N5O2S: 393. 1H NMR (400 MHz, Chloroform-d) delta ppm 2.28 (s, 3 H) 3.84 (q, J=6.06 Hz, 2 H) 3.93 (s, 3 H) 4.55 (t, J=6.06 Hz, 2 H) 6.56 (d, J=5.48 Hz, 1 H) 6.93 – 6.98 (m, 2 H) 7.02 (t, J=5.67 Hz, 1 H) 7.16 (d, J=I .17 Hz, 1 H) 7.46 (d, J=2.74 Hz, 1 H) 7.52 (d, J=9.78 Hz, 1 H) 8.40 (d, J=2.74 Hz, 1 H) 8.46 (d, J=5.28 Hz, 1 H).

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine

Reference£º
Patent; AMGEN INC.; WO2008/103277; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO110,mainly used in chemical industry, its synthesis route is as follows.,1309774-03-5

0386-2> A mixture of 7-bromo-2-chloro-1,5-naphthyridine (182 mg), bis(pinacolato)diboron (286 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (61 mg), potassium acetate (147 mg), and 1,4-dioxane (4 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 3-Ethyl-4-iodo-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazole (250 mg), sodium carbonate (158 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (53 mg), and water (0.4 mL) were added thereto, followed by stirring at 80 C. for 3 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 2-chloro-7-(3-ethyl-1-(3-(pyrrolidin-1-yl)propyl)-1H-pyrazol-4-yl)-1,5-naphthyridine (161 mg). MS m/z (M+H): 370.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine,belong naphthyridine compound

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

Name is 3-Bromo-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 17965-71-8, its synthesis route is as follows.,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).

With the complex challenges of chemical substances, we look forward to future research findings about 3-Bromo-1,5-naphthyridine

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