Heterocyclic Building Blocks-Naphthyridine

253-72-5, 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. 1,6-Naphthyridine, cas is 253-72-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

2. 6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridine 1,6-Naphthyridine (13.7 g, 105 mmol) and benzyl bromide (36.05 g, 210 mmol) were combined in acetonitrile (200 ml) and heated to reflux until no 1,6-naphthyridine was visible by thin layer chromatography. After removal of the solvent in vacuo, the residue was washed several times with ether and dissolved in methanol (700 ml). Water (250 ml) was added, and the solution cooled to 0¡ã; portionwise addition of sodium borohydride (20.8 g, 550 mmol) brought about vigorous gas evolution and a slight rise in temperature. The reaction mixture was allowed to warm to room temperature and stir for 18 hours. The solvent was then removed in vacuo and the residue partitioned between water (750 ml) and methylene chloride (300 ml). The aqueous layer was extracted with additional methylene chloride (2*300 ml) and the combined organic extracts were washed once with water and once with saturated aqueous sodium chloride. Removal of solvent provided a dark amber foam, which was purified by column chromatography (99:1 methylene chloride:methanol) to yield the title product (12.1 g, 54 mmol, 51percent yield).

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 1,6-Naphthyridine, 253-72-5

Reference£º
Patent; Pfizer Inc.; US5037834; (1991); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

23616-31-1, 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. 1,6-Naphthyridin-5(6H)-one, cas is 23616-31-1,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A suspension of XI-3 (2.36 g, 15.7 mmol, 1 eq), N-bromosuccinimide (3.1 g, 17.3 mmol, 1 eq), and 50 mL of 1,2-dichloroethane was stuffed at rt for 3.5 hrs. The mixture was filtered; the solids were washed successively with small amounts of chloroform, water, and diethyl ether, and then dried to leave XI-4 (0.8 g, 23percent yield). MS (ES) m/z (M+H) 226.8.

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 1,6-Naphthyridin-5(6H)-one, 23616-31-1

Reference£º
Patent; INTERMUNE, INC.; RAMPHAL, Johnnie, Y.; BUCKMAN, Brad, Owen; EMAYAN, Kumaraswamy; NICHOLAS, John, Beamond; SEIWERT, Scott, D.; WO2015/153683; (2015); A1;,
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1,8-Naphthyridine | C8H6N2 – PubChem

254-79-5, 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. 1,5-Naphthyridine, cas is 254-79-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

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).

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 1,5-Naphthyridine, 254-79-5

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;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

10261-82-2, 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. 1,5-Naphthyridin-2(1H)-one, cas is 10261-82-2,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

A 250 mL round bottomed flask charged with 1,5-naphthyridin-2(1H)-one (2.98 g, 20.37 mmol) and phosphorus oxychloride (40 ml, 437 mmol) was heated at 100 C. for 3 h. The reaction was cooled to room temperature and excess POCl3 was removed in vacuo. The residue was poured onto ice and neutralized with NaHCO3. The mixture was extracted with DCM (4*) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (ISCO (80 gram)) eluting with EtOAc:DCM (0:1?1:4) to give 1.08 g (32%, 2 steps) of a light-yellow amorphous solid. ESI-MS 164.9, 166.9 [M+1].

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 1,5-Naphthyridin-2(1H)-one, 10261-82-2

Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

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

A. 1.1 g (12.8 mmol) of pivalaldehyde are added to 0.86 g (10 mmol) of 3-amino-pyrrolidine at room temperature and after 1 hour the mixture is diluted with 20 ml of acetonitrile and 10 ml of dimethylformaldehyde. 1.1 g (10 mmol) of 1,4-diazabicyclo-[2.2.2]octane and 3.8 g (10 mmol) of ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate are added and the mixture is stirred overnight at room temperature. The precipitate is filtered off with suction, washed with water and dried in vacuo at 100 C. Yield: 4.25 g (85% of theory) of ethyl 1-(2,4-difluorophenyl)-7-[3-(2,2-dimethyl-propylidene-amino)-1-pyrrolidinyl]-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate of melting point: 197-198 C. (with decomposition). 1 H-NMR (CDCl3): delta 1.05 s (9H), 1.4 t (3H), 1.9 m und2.05 m (2H), a broad m at 3.5-3.7 (6H), 4.4 q (2H), 7.05 m (2H), 7.4 m (1H), 8.05 d (1H), 8.35 ppm s (1H).

With the complex challenges of chemical substances, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reference£º
Patent; Bayer Aktiengesellschaft; US5061712; (1991); A;,
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

Example 1.1.1 and Example 1.1.2: 3-Bromo-[1 ,5]naphthyridine-5-oxide and 3- bromo-1 ,5-naphthyridine-1 -oxide4.43 g (21.2 mmol, 1 eq) of 3-bromo-1 ,5-naphthyridine (W. Czuba, Recueil des Travaux Chimiques des Pays-Bas 1963, 82, 988-996) were introduced in 165 ml. of methylene chloride. 5.23 g (21.2 mmol, 1 eq) of mefa-chloroperbenzoic acid were then added portionwise at 0 C. The mixture was stirred at rt for 18 h. The mixture was washed with 1 M aqueous NaOH solution and water. Organic layer was dried over Na2S04, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 3.08 g of 3-bromo-1 ,5- naphthyridine-5-oxide (pale yellow powder) with 64% yield and 1.00 g of 3-bromo-1 ,5- naphthyridine-1 -oxide (yellow powder) with 21 % yield.3-Bromo-[1 ,5]naphthyridine-5-oxideYield: 3.08 g (64 % of theory). m.p.: 148-149 C.1H-NMR (DMSO-d6, 400 MHz): delta = 9,21 (d, 1 H); 9, 10 (d, 1 H); 8,75 (d, 1 H); 8,06 (d, 1 H); 7,80 (dd, 1 H) ppm. MS: m/z 226 (M+H+).3-Bromo-[1 ,5]naphthyridine-1 -oxide Yield: 1.00 g (21 % of theory), m.p.: 153-154 C.1H-NMR (DMSO-d6, 400 MHz): delta = 9, 12 (d, 1 H); 9,03 (s, 1 H); 8,86 (d, 1 H); 8,36 (s, 1 H); 7,94 (dd, 1 H) ppm.MS: m/z 226 (M+H+).

With the complex challenges of chemical substances, we look forward to future research findings about 17965-71-8,belong naphthyridine compound

Reference£º
Patent; AeTERNA ZENTARIS GMBH; WO2011/64250; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 1,8-Naphthyridine-2-carboxylic acid, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 215523-34-5, its synthesis route is as follows.,215523-34-5

General procedure: To the resin 13 (560 mg) in DMF (2.5 mL) were added a solutionof the appropriate Fmoc-protected amino acid (see Tables 1-3)(0.3 M), PyBOP (0.3 M) and HOBt (0.3 M) in dry DMF (4.2 mL). Thesuspensions were stirred for 3 min and then DIPEA (0.6 M) wasadded. The suspensions were stirred for 3 h under an argon atmosphereat rt. The resins were washed successively with DCM(150 mL), MeOH (120 mL), DCM (75 mL) and dried overnight undervacuum to give resins 14, each bearing an appropriate Fmoc-protectedamino acid. To the resins 14 (161 mg, 0.13 mmol) wereadded a solution of piperidine (20%, v/v) in DCM (2.1 mL) and themixtures were stirred for 1 h at rt. After filtration, the resins werewashed successively with DCM (50 mL), MeOH (45 mL), DCM(25 mL) and dried under vacuum to give resins 15. Portions(65 mg) of resins 15 were placed in reactor wells (12 mL) of anautomated synthesizer reaction block (40-well format) (AdvancedChemTech). To each well was added a solution of appropriate carboxylicacid (see Tables 1-3) (0.3 M), PyBOP (0.3 M) and HOBt 6-Cl(0.3 M) and DIPEA (0.6 M) in dry DMF (2 mL). The suspensionswere vortexed at 300 rpm over a period of 5 h under an argonatmosphere. The wells were then filtered to remove the reactivesolution from the resins 16 and washed successively with THF,DCM, MeOH and DCM.

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

Reference£º
Article; Talbot, Amelie; Maltais, Rene; Kenmogne, Lucie Carolle; Roy, Jenny; Poirier, Donald; Steroids; vol. 107; (2016); p. 55 – 64;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Name is 7-Bromo-2-chloro-1,5-naphthyridine, as a common heterocyclic compound, it belongs to naphthyridine compound, and cas is 1309774-03-5, its synthesis route is as follows.,1309774-03-5

Example 0757 0757-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (600 mg), 1,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (442 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (174 mg), sodium carbonate (522 mg), 1,4-dioxane (24 mL), and water (2.4 mL) was stirred at 100 C. for 3 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. The reaction residue was purified by silica gel column chromatography (chloroform-methanol, NH silica), thereby obtaining 2-chloro-7-(1,3-dimethyl-1H-pyrazol-4-yl)-1,5-naphthyridine (412 mg) as a white solid. MS m/z (M+H): 259.

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

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

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.

952059-69-7, (6- (3-methylisothiazol-5-yl) – [1,2,4] triazolo [4, 3-b] pyridazin-3- yDmethanamine (548 mg, 2225 mumol) and 8-chloro-3-methoxy-l, 5- naphthyridine (576 mg, 2959 mumol) were charged in a microwave vial. 2-butanol (7 mL) was added and the reaction mixture was stirred at 1200C under micro-waves irradiation for 8h. 2M NH3 in MeOH was added. Purification by MPLC (DCM/MeOH+l%NH4OH: 100/0 to 90/10) afforded the title compound (720 mg, 80% yield). MS m/z = 405.1 [M+H]+. Calc’d for C19H16N8OS: 404.46

As the paragraph descriping shows that 952059-69-7 is playing an increasingly important role.

Reference£º
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
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

A 0.5 – 2 mL microwave vial was charged with 1- (4- (3- (aminomethyl) – [1,2,4] triazolo [4, 3-b] pyridazin-6-yl) -2- fluorophenyl)pyrrolidin-2-one (0.0792 g, 0.243 mmol), 8-chloro- 3-methoxy-l, 5-naphthyridine (0.0590 g, 0.303 mmol), and butan- 2-ol (1.00 ml, 0.243 mmol), sealed, then placed in a Personal Chemistry Microwave for 4 hours at 1200C. The mixture was concentrated, then triturated with MeOH to give 1- (2-fluoro-4- (3- ( (7-methoxy-l, 5-naphthyridin-4-ylamino) methyl) – [1,2,4] triazolo [4, 3-b] pyridazin-6-yl) phenyl)pyrrolidin-2-one as the hydrochloric salt .MS (ESI pos. ion) m/z: 485 (MH+). Calc’d exact mass for C25H2IFN8O2: 484.

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

Reference£º
Patent; AMGEN INC.; WO2008/8539; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem