Heterocyclic Building Blocks-Naphthyridine

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2,5-Dichloro-1,8-naphthyridine, and cas is 91870-15-4, its synthesis route is as follows.,91870-15-4

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).

91870-15-4 is used more and more widely, we look forward to future research findings about 2,5-Dichloro-1,8-naphthyridine

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 quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO185,mainly used in chemical industry, its synthesis route is as follows.,952059-69-7

General procedure: (Method C5) Synthesis of N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine A pyrex reaction tube was charged with 8-chloro-3-methoxy-1,5-naphthyridine (50 mg, 0.26 mmol), 5-(4-phenylphthalazin-1-ylamino)pyridin-2-ol (80 mg, 0.26 mmol), cesium carbonate (249 mg, 0.76 mmol) and DMSO (2 mL). The tube was sealed and the reaction mixture was heated to 130 C. After 3.5 h, an aliquot was analyzed by LCMS, and the desired product was determined to be the major peak. The reaction mixture was diluted with DMSO and purified by Gilson HPLC {5-65% (0.1% TFA in CH3CN) in H2O over 20 min}. The product-containing fractions were combined, basified by addition of aq. NaHCO3 and extracted with DCM. The organic portion was dried with Na2SO4, filtered, and concentrated to afford material that was further purified by silica gel chromatography, 90/10/1 CH2Cl2/MeOH/NH4OH. This provided N-(6-(7-methoxy-1,5-naphthyridin-4-yloxy)pyridin-3-yl)-4-phenylphthalazin-1-amine as pure material. MS [M+H]=473.01.48 minutes. Calc’d for C28H20N6O2: 472.5.

With the complex challenges of chemical substances, we look forward to future research findings about 8-Chloro-3-methoxy-1,5-naphthyridine,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 belongs to naphthyridine compound, name is 2-Chloro-1,5-naphthyridine, and cas is 7689-62-5, its synthesis route is as follows.,7689-62-5

EXAMPLE 3 Ethyl 3-(1,5-naphthyridin-2-yl)prop-2-enoate (H1) 2-chloro-1,5-naphthyridine (101 mg, 0.614 mmol), boronate ester B1 (195 mg, 0.920 mmol), S-Phos (25.2 mg, 0.061 mmol), K3PO4 (391 mg, 1.841 mmol) and PdOAc2 (6.89 mg, 0.031 mmol) were combined in a 5-mL microwave vial in THF (2.5 mL) and water (500 mul). The reaction mixture was heated at 100 C for 15 min. The reaction mixture was diluted with EtOAc (20 mL), washed with sat. aq. NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (10 to 100% EtOAc in hexanes) to afford the title compound as a pale orange solid (118 mg, 90%). 1H NMR (500 MHz, DMSO): delta 9.02 (dd, J = 4.1, 1.6 Hz, 1 H), 8.48 (d, J = 8.8 Hz, 1 H), 8.48-8.42 (m, 1 H), 8.25 (d, J = 8.7 Hz, 1 H), 7.84-7.79 (m, 2 H), 7.13 (d, J = 16.0 Hz, 1 H), 4.25 (q, J = 7.1 Hz, 2 H), 1.30 (t, J = 7.1 Hz, 3 H) ppm; LRMS m/z (M+H) 229.2 found, 229.1 required.

With the complex challenges of chemical substances, we look forward to future research findings about 7689-62-5,belong naphthyridine compound

Reference£º
Patent; Merck Sharp & Dohme Corp.; COX, Christopher D.; RAHEEM, Izzat T.; SCHREIER, John D.; (63 pag.)EP2621926; (2017); B1;,
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.

To a solutionof 3-amino-3-pyrrolidin-3-yl-propionitrile (200 mg, 1.44 mmol) and7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydro-[l,8] naphthyridine-3-carboxylic acid(282 mg, 1.00 mmol) in acetonitrile (10mL) was added triethylamine (505 mg, 5.00 mmol) and the solution was heated at 80 C for 17 hours. The precipitate was collected by vacuum filtration and rinsed with acetonitrile. The solid was dried overnight at 45 C under vacuum to give 240 mg of the title compound (yield: 62%). MS (APCI+):mAz 386 (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; WARNER-LAMBERT COMPANY LLC; WO2005/49602; (2005); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 1,8-Diazanaphthalene, and cas is 254-60-4, its synthesis route is as follows.,254-60-4

Step D Preparation of 3-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-N-Boc-propylamine (1-5) A solution of naphthyridine 1-4 (2.72 g) in methanol (20 mL) was hydrogenated in the presence of 5% rhodium on carbon (2.1 g; containing 63% of water) under 40 psi of hydrogen at 5 C. for 10 hours. The catalyst was filtered through Solka Flok and washed with methanol (25 mL twice). The filtrate and washings were combined, concentrated in vacuo, and dissolved in methanol (6.8 mL). To the solution was added water (6.8 mL) slowly at ambient temperature. The resulting solid was collected by filtration, washed with a mixture of water and methanol (2:1; 5 mL), and dried under vacuum to give the desired crystalline tetrahydronaphthyridine 1-5 (1.9 g). The mother liquor yielded an additional 5% of 1-5; m.p. 95.2-96.3 C. 1H NMR (400 MHz; CDCl3): delta 7.05 (d, J=7.4 Hz, 1H), 6.33 (d, J=7.3 Hz, 1H), 5.45 (bs, 1H), 4.92 (bs, 1H), 3.39 (m, 2H), 114 (s, 9H); J=7.3, 2H), 1.89 (m, 2H), 1.83 (m, 2H), 1.44 (s, 9H); 13C NMR (101 MHz; CDCl3): delta157.1, 156.0, 155.4, 136.7, 113.4, 111.3, 78.6, 41.4, 40.3, 35.0, 29.4, 28.4, 26.2, 21.3.

With the complex challenges of chemical substances, we look forward to future research findings about 1,8-Diazanaphthalene

Reference£º
Patent; Merck & Co., Inc.; US6423845; (2002); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

3-Bromo-1,5-naphthyridine, cas is 17965-71-8, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.,17965-71-8

Nitrogen was flushed into a stirred solution of 3-bromo-1,5-naphthyridine (2 g, 9.56 mmol) in dry toluene for 15min. 1-Ethoxy vinyl tributyltin (3.8 g, 10.52 mmol) and Bis(triphenylphosphine)palladium chloride (0.33 g, 4.7 mmol) were added and the mixture was stirred overnight at 90 C. The reaction mixture was cooled to rt and filtered through celite. The filtrate was concentrated under vacuum. 6N HCI (50 mL) was added to the resulting mixture and the solution was stirred for 1 h at rt. It was then neutralized with a saturated solution of NaHCO3. It extracted with EtOAc (3 x 150 mL). Combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under vacuum to get crude product. The crude was purified by flash column chromatography to afford the title compound. Yield: 62% (1.0 g, yellow solid). 1H NMR (400 MHz, DMSO-de): delta 9.39 (d, J = 2.8 Hz, 1 H), 9.14-9.12 (m, 1 H), 8.96 (d, J = 2.4 Hz, 1 H), 8.51 (d, J = 11.6 Hz, 1 H), 7.93-7.89 (m, 1 H), 7.65-7.54 (m, 1 H), 2.50 (d, J = 2.4 Hz, 3H). LCMS: (Method A) 173.2 (M +H), Rt. 1.63 min, 90.89% (Max).

17965-71-8 is used more and more widely, we look forward to future research findings about 3-Bromo-1,5-naphthyridine

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut Gajendra; (247 pag.)WO2017/144639; (2017); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,5,7-Dichloro-1,6-naphthyridine,337958-60-8,Molecular formula: C8H4Cl2N2,mainly used in chemical industry, its synthesis route is as follows.,337958-60-8

To an ice cooled solution of 1 ,1-dimethylethyl (3S)-3-fluoro-3-(hydroxymethyl)-1 – piperidinecarboxylate (1.406g, 6.03mmol) in DMF (20ml) was added sodium hydride (0.313g, 7.84mmol) (60% dispersion in mineral oil). This was stirred for 15min before adding 5,7-dichloro-1 ,6-naphthyridine (1 .2g, 6.03mmol). This was warmed to room temp and stirred for 4h. The reaction had gone to completion and so was cautiously quenched with aqueous ammonium chloride before partitioning between aqueous ammonium chloride and ethyl acetate. The layers were separated and the aqueous was re-extracted with ethyl acetate. The combined organics were washed with brine and concentrated in vacuo to give the crude product. This was dissolved in DCM and purified through silica (50g), eluting with a gradient of 0-50% ethyl acetate in DCM. Appropriate fractions were concentrated in vacuo to yield the title compound as a cream foamy gum (1.91 g).LCMS: Rt = 1.18min, MH+ = 395.85

With the synthetic route has been constantly updated, we look forward to future research findings about 5,7-Dichloro-1,6-naphthyridine,belong naphthyridine compound

Reference£º
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander George Steven; WILSON, David Matthew; WO2011/134971; (2011); A1;,
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: C8H14ClNO4,mainly used in chemical industry, its synthesis route is as follows.,10261-82-2

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].

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

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO263,mainly used in chemical industry, its synthesis route is as follows.,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.

With the synthetic route has been constantly updated, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine,belong naphthyridine compound

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

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

a 2-Methyl-8-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,8-naphthyridine A mixture of 2-methyl-1,8-naphthyridine (J. Chem. Soc. (C) 1966, 315; 5.13 g, 35.58 mmole), 10percent Pd/C (1.14 g, 1.07 mmole), and absolute EtOH (70 mL) was deoxygenated through three evacuation/H2 purge cycles, then was stirred briskly under a balloon of H2. After 18.5 hr, the mixture was filtered through celite.(R)., and the filter pad was washed sequentially with absolute EtOH and EtOAc. The filtrate was concentrated to dryness, and the residue was reconcentrated from EtOAc to leave an off-white solid (5.25 g). A solution of the above material (5.25 g), di-tert-butyl dicarbonate (15.53 g, 71.16 mmole), and CH2Cl2 (10 mL) was concentrated on the rotavap to remove the solvent, and the oily residue was heated under N2 in an oil bath set at 55-60¡ã C. After 45 hr, the reaction was cooled to RT, and the residue was flash chromatographed on silica gel (40percent EtOAc/hexanes). The title compound (4.90 g, 55percent) was obtained as a light yellow solid: 1H NMR (300 MHz, CDCl3) delta7.27 (d, J=7.6 Hz, 1H), 6.81 (d, 7.6 Hz, 1H), 3.69 -3.79 (m, 2H), 2.65-2.75 (m, 2H), 2.48 (s, 3H), 1.83-1.98 (m, 2H), 1.52 (s, 9H), MS (ES) m/e 249 (M+H)+.

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

Reference£º
Patent; SmithKline Beecham Corporation; US6495560; (2002); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem