Month: October 2020

1260670-05-0, 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. 3-Bromo-8-chloro-1,7-naphthyridine, cas is 1260670-05-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Parallel preparation of examples 6-7: To a set of vials containing the requisite aryl halide (0.20 mmol) was added a solution of HI (50 mg, 0.10 mmol) in THF (1.0 mL). The vials were capped and transferred into a glove box under an atmosphere of nitrogen. To each vial was then added a solution of LHMDS (1.0 M in THF, 0.25 mL, 0.25 mmol). The mixtures were then heated at 50 C with stirring overnight. After that time, water (2 mL) and DCM (2 mL) were added to each vial. The mixtures were transferred to a set of fritted barrel filters. The organic layer from each vial was drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. To each vial was then added water (0.050 mL) and TFA (0.5 mL). The mixtures were stirred at 50C with stirring overnight. After that time, the mixtures were concentrated in vacuo. The crude residues were dissolved in DMSO (1 mL) and filtered. The crude residue containing Example 6 was purified by mass triggered preparative HPLC. [column: Waters XBridge CI 8, 5mupiiota , 19×100 mm; solvent: gradient 35-70% MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min; 8 min run time] to afford Example 6. The crude residue containing Example 7 was purified by mass triggered preparative HPLC [Waters Sunfire CI 8 column, 5muetaiota, 19 100 mm, using a gradient from 10% initial to 45% final MeCN (0.1% TFA) in water (0.1% TFA), 25 mL/min, 8 min run time] to afford Example 7.

The chemical industry reduces the impact on the environment during synthesis,1260670-05-0,3-Bromo-8-chloro-1,7-naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; CUMMING, Jared, N.; SCOTT, Jack, D.; (65 pag.)WO2016/40226; (2016); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 96568-07-9 its synthesis route is as follows.

EXAMPLE 62 Ethyl 1-cyclopropyl-6-fluoro-7-[3-(1,2,3-triazol-1-yl]piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 3-(1,2,3-triazol-1-yl)piperidine (150 mg, 0.96 mmol) was added to a solution of ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.48 mmol) in a mixture of acetonitrile (10 ml) and pyridine (3 ml). The reaction mixture was heated at 100 C. for 6 hrs and then concentrated to dryness. The residue was diluted with water and thus solid separated was filtered, washed thoroughly with water and dried. Yield 90 mg, m.p. 205-206 C.; 1 H NMR (CDCl3) delta: 8.58 (s, 1H), 8.15 (d, 1H), 7.78 (s, 1H), 7.65 (s, 1H), 4.90 (m, 2H), 4.40 (m, 3H), 3.45 (m, 3H), 1.75-2.50 (m, 4H), 1.40 (t, 3H), 0.95-1.35 (m, 4H).

96568-07-9, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,96568-07-9 ,Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; SynPhar Laboratories, Inc.; US5342846; (1994); A;,
1,8-Naphthyridine – Wikipedia
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.

Example la: Synthesis of 3-bromo-l,5-naphthyridine (C-2) [00305] 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. lR NMR (300 MHz, CDC13- (5) delta: 8.97 (m, 2H), 8.57 (s, 1H), 8.37 (d, J = 8.4 Hz, 1H), 7.65 (m, 1H); ESI-MS m/z : 208.96 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis,254-79-5,1,5-Naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; INTELLIKINE, LLC; REN, Pingda; LI, Liansheng; CHAN, Katrina; WO2013/78441; (2013); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, and cas is 100361-18-0, its synthesis route is as follows.

Triethylamine (5.1 LLLT) was added to 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1, 4- DIHYDRO-1, 8-naphthyridine-3-carboxylic acid (3.05 g) in water (25 MNo.) at 15-20 C, and the mixture was stirred for 20 minutes. Compound (I) (3.86 g) prepared in Example 1 and water (5 N) were added, and this mixture was stirred at 20-25 C for 18 hours. The product thus obtained was filtered, and the filter cake was washed with water (30 UP.) and ethanol (30 INL),). Drying at 50 C under vacuum gave the title compound (4.23 g) as a white solid. The identification data were the same as those of the authentic sample.

100361-18-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,100361-18-0 ,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; LG LIFE SCIENCES LTD.; WO2004/92129; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

17965-71-8, 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. 3-Bromo-1,5-naphthyridine, cas is 17965-71-8,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

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+).

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 3-Bromo-1,5-naphthyridine, 17965-71-8

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

It is a common heterocyclic compound, the naphthyridine compound, 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, cas is 100361-18-0 its synthesis route is as follows.

7-F4- (2-HVDROXVETHYLIDENE) PIPERIDIN-1-YLL-1-CVCLOPROPVL-6-FLUORO-4-OXO-1, 4- DIHVDRONAPHTHYRIDINE-3-CARBOXVIIC acid (163) A solution of amine 103 (256 mg, 1.06 MMOL) and triethylamine (0.5 mL, 3.55 MMOL) in ACETONITRILE (4 mL) was treated with 7-CHLORO-1-CYCLOPROPYL-6-FLUORO-4-OXO-1, 4-dihydro-naphthyridine-3- carboxylic acid (200 mg, 0.71 MMOL) under nitrogen and the reaction mixture was allowed to stir for 16 h. The resulting mixture was concentrated in vacuo, and the residue was washed with water (3 x 10 mL) and allowed to dry overnight to afford the title compound 163 (105 mg, 40%). MS 374 (M+H).

100361-18-0, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,100361-18-0 ,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/33108; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

952059-69-7, 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. 8-Chloro-3-methoxy-1,5-naphthyridine, cas is 952059-69-7,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of tert- butyl (6-bromo- [1,2,4] triazolo [4 , 3 -a] pyridin-3- yUmethylcarbamate (0.900 g, 2.75 mmol) in CH2Cl2 (10 mL) was added TFA (0.848 ml, 11.0 mmol) and the mixture stirred at rt. After 30 minutes additional TFA (0.848 ml, 11.0 mmol) was added, and the mixture stirred at rt 2 h more then concentrated. The residue was taken up into 2-butanol (5 mL) and combined with 8-chloro-3-methoxy-l, 5-naphthyridine (0.535 g, 2.75 mmol) in a 5 mL microwave vessel. The vessel was sealed and the mixture heated in the microwave for 10 min at 120 C with a 60 sec prestir. The mixture was concentrated, diluted with DCM and stirred with 2N NaOH (pH 14) for 30 minutes. The solid was filtered to afford the title compound as a beige solid.

The chemical industry reduces the impact on the environment during synthesis,952059-69-7,8-Chloro-3-methoxy-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

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

1309774-03-5, 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. 7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

0399-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (48 mg), bis(pinacolato)diboron (60 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (16 mg), potassium acetate (39 mg), and 1,4-dioxane (2 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. 4-(4-Iodo-1H-pyrazol-1-yl)pyridine (75 mg), sodium carbonate (42 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (14 mg), and water (0.2 mL) were added thereto, followed by stirring at 80 C. for 8 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-hexane), thereby obtaining 2-chloro-7-(1-(pyridin-4-yl)-1H-pyrazol-4-yl)-1,5-naphthyridine (29 mg). MS m/z (M+H): 308.

The chemical industry reduces the impact on the environment during synthesis,1309774-03-5,7-Bromo-2-chloro-1,5-naphthyridine,I believe this compound will play a more active role in future production and life.

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

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 (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.

The chemical industry reduces the impact on the environment during synthesis,1569-16-0,2-Methyl[1,8]-Naphthyridine,I believe this compound will play a more active role in future production and life.

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
1,8-Naphthyridine | C8H6N2 – PubChem

91870-15-4, 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. 2,5-Dichloro-1,8-naphthyridine, cas is 91870-15-4,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.

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 chemical industry reduces the impact on the environment during synthesis,91870-15-4,2,5-Dichloro-1,8-naphthyridine,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; ABBOTT LABORATORIES; WO2008/133753; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem