Heterocyclic Building Blocks-Naphthyridine

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

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

(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

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.; WO2008/8539; (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: C8H14ClNO8,mainly used in chemical industry, its synthesis route is as follows.,10261-82-2

To suspension of 1,5-naphthyridin-2(1H)-one (0.200 g, 1.368 mmol) in Pyridine (1 mL) was added slowly trifluoromethanesulfonic anhydride (0.050 mL, 0.298 mmol). After the addition, the reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated under high vacuum and residue diluted with water and extracted with EtOAc. EtOAc was washed with water, brine, dried over Na2SO4 and concentrated to give crude 1,5-naphthyridin-2-yl trifluoromethanesulfonate. To this crude 1,5-naphthyridin-2-yl trifluoromethanesulfonate (100 mg) in DMSO (0.5 mL) was added 7-(trans-3-aminocyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one hydrochloride, INTERMEDIATE 62, (0.05 g, 0.186 mmol) and N,N-diisopropylethylamine (0.032 mL, 0.186 mmol). The mixture was heated to 100 C. for 2 hours, diluted with water and extracted with EtOAc. EtOAc was concentrated and residue purified with ISCO using silical gel column eluting with 0-100% EtOAc/hexanes to give the title compound 7-(trans-3-((1,5-naphthyridin-2-yl)amino)cyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.048 g, 0.133 mmol, 71.6% yield). m/z: 361.2; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.85 (s, 1H) 8.62 (dd, J=4.21, 1.27 Hz, 1H) 8.33 (s, 1H) 8.07 (d, J=9.00 Hz, 1H) 7.98 (d, J=8.22 Hz, 1H) 7.45 (dd, J=8.51, 4.21 Hz, 1H) 6.88 (d, J=9.00 Hz, 1H) 5.46 (d, J=4.50 Hz, 1H) 5.17-5.35 (m, 1H) 4.79 (dd, J=7.92, 3.62 Hz, 1H) 3.32-3.58 (m, 2H) 2.44 (tt, J=10.03, 3.08 Hz, 2H) 1.45 (s, 6H).

With the synthetic route has been constantly updated, we look forward to future research findings about 1,5-Naphthyridin-2(1H)-one,belong naphthyridine compound

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

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.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid

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

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

With the rapid development of chemical substances, we look forward to future research findings about 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid

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

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

Example 0646 0646-1 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (5.0 g), 1-tert-butoxycarbonyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (6.04 g), sodium carbonate (4.4 g), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (366 mg), 1,4-dioxane (24 mL), and water (2.4 mL) was stirred at 110 C. for 5 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, water was added thereto, and the solid matter was collected by filtration. The obtained solid matter was suspended by the addition of ethyl acetate, and the solid matter was collected by filtration, thereby obtaining 2-chloro-7-(1H-pyrazol-4-yl)-1,5-naphthyridine (2.6 g) as a pale brown solid. MS m/z (M+H): 231., 1309774-03-5

With the rapid development 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

254-60-4, 1,8-Diazanaphthalene is a naphthyridine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step C 2-Chloro-3-cyclopropyl-[1,8]naphthyridine (2-5) A mixture of naphthyridine 2-4 (14 g, 77 mmol) and 100 mL POCl3 and 0.1 mL DMF was refluxed at 120 C. for 3 hr and concentrated. The residue was treated with 300 mL ice-water and solid K2CO3 until pH=9. The mixture was extracted three times with ethyl acetate, washed with brine and dried over MgSO4. After solvent removal, the desired compound 2-5 was obtained as a yellowish solid. 1H NMR (400 MHz, CDCl3): delta9.00 (q, 1H), 8.10 (q, 1H), 7.78 (s, 1H), 7.50 (q, 1H), 2.34 (m, 1H), 1.00 (m, 2H), 0.82 (m, 2H).

254-60-4, As the paragraph descriping shows that 254-60-4 is playing an increasingly important role.

Reference£º
Patent; Wang, Jiabing; US2004/38963; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem