Heterocyclic Building Blocks-Naphthyridine

215523-34-5, 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. 1,8-Naphthyridine-2-carboxylic acid, cas is 215523-34-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

14.00 mmol of corresponding amino derivative and 10.00 mmol of carboxylic acid, 11.00 mmol of 1-hydroxybenzotriazole and 11.10 mmol of N’-(3-dimethylaminopropyl)-N-ethylcarbodiimid hydrochlorid in 120 cm3 N,N dimethylformamide was stirred overnight at room temperature. Then 1000 g of crashed ice was added and stirred further one hour. The precipitate was filtered off, washed with saturated NaHCO3 solution, water and dried at room temperature. The crude material was refluxed in ethylalcohol for 10 minutes, cooled back and filtered off.

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-Naphthyridine-2-carboxylic acid, 215523-34-5

Reference£º
Patent; Klebl, Bert; Baumann, Matthias; Hoppe, Edmund; Brehmer, Dirk; Daub, Henrik; Keri, Gyorgy; Varga, Zoltan; Marosfalvi, Jeno; Orfi, Laszlo; US2008/187575; (2008); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

15944-34-0, 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-1,8-naphthyridin-2-ol, cas is 15944-34-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 7-chloro-1 ,8-naphthyridin-2(1 H)-one (700 mg, 3.9 mmol) in MeOH (15 mL), NaOMe (25% solution in MeOH, 20 mL) was added. The resulting solution was stirred at reflux for 15 h then thesolvent was removed in vacuo. Water (100 mL) and EtOAc (80 mL) were added, the phases were separated and the aqueous layer was extracted with EtOAc (8 x 80 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (630 mg, 3.6 mmol, 92% yield). LC-MS (M-H) = 177.2

The chemical industry reduces the impact on the environment during synthesis,15944-34-0,7-Chloro-1,8-naphthyridin-2-ol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; MAGARO’, Gabriele; GAROFALO, Barbara; FURLOTTI, Guido; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; (182 pag.)WO2017/211759; (2017); A1;,
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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.

PREPARATION 11 7-[2-(t-butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid. 400 mg of 1-cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid and 84 g of t-butyl 8-(methoxyimino)-2,6diazaspiro[3,4]octane-2-carboxylate were added to 10 ml of acetonitrile and the resulting mixture was stirred for 3 hours at 45-50 C. Then the precipitated solid was filtered and dried to give 650 mg of the titled compound(yield: 93.9%). m.p.: 278-279 C. 1H-NMR(CDCl3, ppm): 1.05(m, 2H), 1.27(m, 2H), 1.45(s, 9H), 3.61~3.67(m, 1H), 3.90(s, 3H), 3.94(s, 2H), 4.25(s, 2H), 4.27(s, 2H), 4.56(s, 2H), 8.04(d, 1H, J=11.71 Hz), 8.68(s,1H).

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; Dong Wha Pharmaceutical Industrial Co., Ltd.; US6313299; (2001); B1;,
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-1 ,8-naphthyridine (3.0 g, 20.7 mmol) in CH2CI2 (300 ml) was added Lambda/-chlorosuccimide (11.1 g, 81.6 mmol) and AIBN (15 mg). The reaction was refluxed for 4h with additional AlBN (7mg) added each hour, followed by reflux for 3Oh. The cooled reaction solution was washed well with aqueous Na2COs, brine, dried over MgSO4, and concentrated to give the desired product (5.12g, 100percent) as a tan solid:LC/MS (ES) m/z 247.2 [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 2-Methyl[1,8]-Naphthyridine, 1569-16-0

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/16610; (2007); A2;,
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Name is 5,7-Dichloro-1,6-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 337958-60-8, its synthesis route is as follows.,337958-60-8

To a20 mL vial was added 5,7-dichloro-1,6-naphthyridine, (289.1 mg, 1.45 mmol), tert-butyl (1R,3s,55)-3-amino-8-azabicyclo[3 .2.1 joctane-8-carboxylate (362 mg, 1.60 mmol), DIPEA (0.76 mL, 4.36 mmol), and DMSO (7.26 mL). The vial was capped and the reaction mixture was heated to 110 C and stirred for 16 h. The reaction mixturewas diluted with water and extracted with EtOAc (3 x 20 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated to afford a brown oil, which was purified by column chromatography (24 g column; 0-80% EtOAc in hexanes) to afford the title product as a pale yellow solid (455.2 mg, 69 % yield; 85% purity). (m/z): [M+Hf? calcd for C20H25C1N402 389.17, 391.16 found 391.5.

With the complex challenges of chemical substances, we look forward to future research findings about 5,7-Dichloro-1,6-naphthyridine

Reference£º
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; HUDSON, Ryan; KOZAK, Jennifer; FATHEREE, Paul R.; PODESTO, Dante D.; BRANDT, Gary E.L.; FLEURY, Melissa; BEAUSOLEIL, Anne-Marie; HUANG, Xiaojun; THALLADI, Venkat R.; (121 pag.)WO2016/191524; (2016); A1;,
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It is a common heterocyclic compound, the naphthyridine compound, 2-Chloro-1,5-naphthyridine, cas is 7689-62-5 its synthesis route is as follows.,7689-62-5

Under Ar(g), to a mixture of pyrazin-2-amine (1) (209mg, 2.2mmol), 2- chloro-1 ,5-naphthyridine (2) (329mg, 2.0mmol), Cs2C03 (1.30g, 4.0mmol) was added degassed dry 1 ,4-dioxane (13ml_). The reaction mixture was then flushed with Ar(g) for 1 min before Pd2(dba)3 (92mg, 0.1 mmol) and Xantphos (127mg, 0.22mmol) were added. The reaction mixture was heated up to 90C for 40h. It was then cooled down to rt and concentrated in vacuo, CH2CI2 (15ml_) and H20 (15ml_) were added. The organic phase was separated and the water layer was extracted with EtOAc (15ml_). The organic layers were combined and Pd- scavenger (MP-TMT, ~400mg, 1.3mmol/g) was added. This was shaken for several hours followed by filtration. The filtrate was concentrated in vacuo, dissolved in DMSO (4ml_) and purified by basic prep LCMS to yield (3) as a solid (121 mg, 27%). (0160) LCMS (ES): Found 224.3 [M+Hf.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Chloro-1,5-naphthyridine

Reference£º
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
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As a common heterocyclic compound, it belongs to naphthyridine compound, name is 3-Bromo-1,7-naphthyridin-8(7H)-one, and cas is 1375301-90-8, its synthesis route is as follows.,1375301-90-8

3-Bromo-7H-[1 ,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCI3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130 C for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1 .1 g, 4.52 mmol).HPLC: RtH9= 0.86 min; ESIMS [M+H]+ = 242.8, 244.8, 246.8 (1 Br,1 CI);1H-NMR (400 MHz, DMSO-d6): delta 9.22 (d, 1 H), 8.95 (2, 1 H), 8.49 (d, 1 H), 7.99 (d, 1 H).

With the complex challenges of chemical substances, we look forward to future research findings about 1375301-90-8,belong naphthyridine compound

Reference£º
Patent; NOVARTIS AG; HURTH, Konstanze; JACQUIER, Sebastien; MACHAUER, Rainer; RUEEGER, Heinrich; TINTELNOT-BLOMLEY, Marina; VEENSTRA, Siem Jacob; VOEGTLE, Markus; WO2013/54291; (2013); A1;,
1,8-Naphthyridine – Wikipedia
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It is a common heterocyclic compound, the naphthyridine compound, 7-Chloro-1,8-naphthyridin-2-ol, cas is 15944-34-0 its synthesis route is as follows.,15944-34-0

Preparation B 7-methoxy-1H-[1,8]naphthyridin-2-one To a solution of 7-chloro-1H-[1,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 mL) was added NaOMe (25 wt % in MeOH, 161 mL). The resulting solution was stirred at reflux for 15 h. The solvent was removed in vacuo. Water (100 mL) and EA (80 mL) were added. The phases were separated and the aq. layer was extracted with EA (8*80 mL). The combined org. layers were washed with brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The title compound was obtained as a beige solid (5.22 g, 100% yield). 1H NMR (d6DMSO) delta: 11.96 (s, 1H); 7.96 (d, J=8.5 Hz, 1H); 7.81 (d, J=9.4 Hz, 1H); 6.63 (d, J=8.5 Hz, 1H); 6.34 (d, J=9.4 Hz, 1H); 3.90 (s, 3H).

With the complex challenges of chemical substances, we look forward to future research findings about 7-Chloro-1,8-naphthyridin-2-ol

Reference£º
Patent; Actelion Pharmaceuticals Ltd.; US2012/40989; (2012); A1;,
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1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,1,6-Naphthyridine-2-carboxylic acid,197507-59-8,Molecular formula: C9H6N2O2,mainly used in chemical industry, its synthesis route is as follows.,197507-59-8

Triethylamine (3.03 ml, 21.8 mmol), ethyl chloroformate (3.73 ml, 39.0 mmol) and 4-dimethylaminopyridine (DMAP) (2.40 g, 19.6 mmol) are added, at O0C, to a solution of l,6-naphthyridine-2-carboxylic acid (138) (Chan, L., Jin, H., Stefanac, T., Lavallee, J.F., Falardeau, G., Wang, W., Bedard, J., May, S. and Yuen, L., J. Med. Chem., 1999, 42, 3023-3025) (1.00 g, 5.75 mmol) in anhydrous dichloromethane (75 ml). After returning to ambient temperature, the reaction mixture is brought to reflux for 5 hours, the solution is evaporated to dryness and then the residue is purified on a column of alumina eluted with ethyl acetate to result in the ester 139 (517 mg, 2.56 mmol). Yield: 45%; Rf: 0.86 (Al2O3, ethyl acetate); melting point: 106-1080C; 1H NMR (400 MHz, CDCl3) d 1.41 (t, 3H, J = 7 Hz), 4.49 (q, 2H, J= 7 Hz), 8.02 (d, IH, J= 6 Hz), 8.21 (d, IH, J= 8.5 Hz), 8.39 (d, IH, J = 8.5 Hz), 8.75 (d, IH, J = 6 Hz), 9.29 (s, IH); 13C NMR (100 MHz, CDCl3) d 14.3, 62.0, 122.4, 122.7, 124.0, 137.2, 147.5, 149.7, 152.3, 152.9, 164.6; IR (KBr) V cm”1 : 1256, 1734; MS (m/z, %) 202 (M+, 3), 158 (18), 130 (100), 102 (15), 75 (22), 51 (16).

With the synthetic route has been constantly updated, we look forward to future research findings about 1,6-Naphthyridine-2-carboxylic acid,belong naphthyridine compound

Reference£º
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); WO2008/12782; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

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.

With the complex challenges of chemical substances, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

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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